Heterocyclic compound and noxious arthropod control composition containing same

Abstract

The present invention provides a compound having an excellent controlling efficacy against harmful arthropods. (In the formula, the symbols have the meanings defined in the description. ) The compound or N-oxide thereof has an excellent controlling effect on harmful arthropods. # imgabs0 #

Description

Technical Field

[0001] This application claims priority and the benefits of Japanese Patent Application No. 2022-158626, filed on September 30, 2022, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a heterocyclic compound and a harmful arthropod control composition containing the heterocyclic compound. Background Art

[0003] Various compounds have been studied for the purpose of controlling harmful arthropods. For example, Patent Document 1 describes that a certain compound has a pest control effect.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 2016 / 129684 Summary of the Invention

[0007] Problems to be solved by the invention

[0008] An object of the present invention is to provide a compound having excellent control effect on harmful arthropods.

[0009] Means for solving problems

[0010] The present invention is as follows.

[0011] [1] A compound represented by formula (I) (hereinafter referred to as Compound N of the present invention) or an N-oxide thereof (hereinafter referred to as Compound (I) or an N-oxide thereof as Compound of the present invention).

[0012] [Chemical Formula 1]

[0013]

[0014] 〔where,

[0015] W represents an oxygen atom or a sulfur atom,

[0016] R 1 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group E, a phenyl group which may be substituted by one or more substituents selected from Group F, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group F, C(O)R 4 、C(O)OR 4 or C(O)NR 4 R 5 ,

[0017] R 4 and R 5 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group F, a 5- or 6-membered heterocyclic group which may be substituted with one or more substituents selected from Group F, or a hydrogen atom,

[0018] R 2 represents a C1-C6 alkyl group, a cyclopropyl group, a cyclopropylmethyl group or an NR 6 R 7 ,

[0019] R 6 and R 7 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, or a hydrogen atom; or

[0020] R 6 and R 7 Together with the nitrogen atom to which they are bound, they may form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group,

[0021] n represents 0, 1 or 2,

[0022] G 1 Represents nitrogen atom or CR 3a ,

[0023] G 2 Represents nitrogen atom or CR 3b ,

[0024] G 3 Represents nitrogen atom or CR 3c ,

[0025] G 4 Represents nitrogen atom or CR 3d ,

[0026] R 3a 、R 3b 、R 3c and R 3d are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group H, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group J, a phenyl group which may be substituted by one or more substituents selected from Group K, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group K, OR 8 NR 8 R 9 NR 8a R9a NR 10 NR 8 R 9 NR 10 OR 9 NR 9 C(O)R 11 NR 10 NR 9 C(O)R 11 NR 9 C(O)OR 12 NR 10 NR 9 C(O)OR 12 NR 9 C(O)NR 13 R 14 NR 10 NR 9 C(O)NR 13 R 14 、N=CHNR 13 R 14 、N=S(O) p R 15 R 16 、C(O)R 11 、C(O)OR 17 、C(O)NR 13 R 14 、C(O)NR 9 S(O)2R 18 , CR 19 =NOR 17 NR 9 CR 10 =NOR 17 、S(O) m R 18 , cyano group, nitro group, hydrogen atom or halogen atom,

[0027] p represents 0 or 1,

[0028] m represents 0, 1 or 2,

[0029] R 8 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group L, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group M, a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from Group M, a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from Group J 2 Phenyl substituted with one or more substituents, which may be selected from Group J 2 substituted with one or more substituents in a 6-membered aromatic heterocyclic group, a hydrogen atom or S(O)2R 18 ,

[0030] R 11 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group C1-C3 ... 2 Phenyl substituted with one or more substituents, which may be selected from Group J 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a hydrogen atom,

[0031] R 12 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion of the phenyl C1-C3 alkyl group may be selected from the group J 2 substituted with one or more substituents in},

[0032] R 13 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom,

[0033] R 14 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group L, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group M, S(O)2R 18 or hydrogen atoms,

[0034] R 15 and R 16 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms,

[0035] R 17 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, which may be selected from Group J 2 phenyl substituted with one or more substituents, or a hydrogen atom,

[0036] R 18 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or may be selected from Group J 2 a phenyl group substituted with one or more substituents,

[0037] R 19 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or an OR 20 NR 21 R 22 or hydrogen atoms,

[0038] R 20represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms,

[0039] R 9 、R 10 、R 21 and R 22 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom,

[0040] R 8a and R 9a Together with the nitrogen atom to which they are bonded, they form a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from group P,

[0041] Q means Q 1 or Q 2 ,

[0042] [Chemical Formula 2]

[0043]

[0044] Z 1 Indicates NR 3j , oxygen atoms or sulfur atoms,

[0045] Z 2 Indicates NR 3k , oxygen atoms or sulfur atoms,

[0046] In Q for Q 1 And Z 1 Indicates NR 3j In the case of X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 3 Represents nitrogen atom or CR 3g ,

[0047] In Q for Q 1 And Z 1 When X represents an oxygen atom, 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 3 Represents nitrogen atom or CR 3g (Excluding the existing X 1 、X 2 and X 3 All represent nitrogen atoms),

[0048] In Q for Q 1 And Z 1When X represents a sulfur atom, 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 3 Represents nitrogen atom or CR 3g (Excluding the existing X 1 、X 2 and X 3 All represent nitrogen atoms),

[0049] In Q for Q 2 And Z 2 Indicates NR 3k In the case of X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 4 Represents nitrogen atom or CR 3h ,

[0050] In Q for Q 2 And Z 2 When X represents an oxygen atom, 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 4 Represents nitrogen atom or CR 3h (Excluding the existing X 1 、X 2 and X 4 All represent nitrogen atoms),

[0051] In Q for Q 2 And Z 2 When X represents a sulfur atom, 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 4 Represents nitrogen atom or CR 3h (Excluding the existing X 1 、X 2 and X 4 All represent nitrogen atoms),

[0052] R 3j represents a methyl group which may be substituted with one or more substituents selected from Group T, a C2-C4 chain hydrocarbon group which may be substituted with one or more substituents selected from Group U, a C5-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group V, a C5-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group K 2C3-C7 cycloalkyl substituted with one or more substituents selected from Group X, phenyl which may be substituted with one or more substituents selected from Group X, 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group X, C(O)R 23 、C(O)OR 24 、C(O)NR 25 R 26 、C(O)NR 27 S(O)2R 28 , CR 29 =NOR 24 or S(O) k R 28 ,

[0053] k represents 0, 1 or 2,

[0054] R 23 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group X, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group X, or a hydrogen atom,

[0055] R 24 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group X, or a hydrogen atom,

[0056] R 25 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom,

[0057] R 26 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group V, or a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group K 2 C3-C7 cycloalkyl substituted with one or more substituents, S(O) v R 28 or hydrogen atoms,

[0058] v represents 0, 1 or 2,

[0059] R 28 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from Group X,

[0060] R 29 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or an OR 30 NR 31 R 32or hydrogen atoms,

[0061] R 30 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms,

[0062] R 27 、R 31 and R 32 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom,

[0063] R 3k represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group Y, which may be selected from group M 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group A 2 Phenyl substituted with one or more substituents, which may be selected from Group A 2 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, C(O)R 52 、C(O)OR 53 、C(O)NR 54 R 55 、C(O)NR 56 S(O)2R 57 , CR 58 =NOR 53 、S(O) t R 57 or hydrogen atoms,

[0064] t represents 0, 1 or 2,

[0065] R 52 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, a C1-C3 alkyl group which may be selected from Group A 2 Phenyl substituted with one or more substituents, which may be selected from Group A 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a hydrogen atom,

[0066] R 53 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may be selected from Group A 2 phenyl substituted with one or more substituents, or a hydrogen atom,

[0067] R 54 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom,

[0068] R 55represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group Y, which may be selected from group M 2 C3-C7 cycloalkyl substituted with one or more substituents, S(O) y R 28 or hydrogen atoms,

[0069] y represents 0, 1, or 2,

[0070] R 57 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or may be selected from Group A 2 a phenyl group substituted with one or more substituents,

[0071] R 58 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or an OR 59 NR 60 R 61 or hydrogen atoms,

[0072] R 59 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms,

[0073] R 56 、R 60 and R 61 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom,

[0074] R 3e 、R 3f 、R 3g and R 3h The same or different from each other, indicating that they can be selected from group B 2 C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from group D 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group E 2 Phenyl substituted with one or more substituents, which may be selected from Group E 2 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, OR 33 NR 33 R 34 NR 33a R 34a NR 35 NR 33 R 34 NR 35 OR 34 NR 34 C(O)R 36 NR 35 NR 34C(O)R 36 NR 34 C(O)OR 37 NR 35 NR 34 C(O)OR 37 NR 34 C(O)NR 38 R 39 NR 35 NR 34 C(O)NR 38 R 39 、N=CHNR 38 R 39 、N=S(O) q R 40 R 41 、C(O)R 36 、C(O)OR 42 、C(O)NR 38 R 39 、C(O)NR 34 S(O)2R 43 , CR 44 =NOR 42 NR 34 CR 35 =NOR 42 、S(O) r R 43 , cyano, nitro, halogen or hydrogen atoms,

[0075] q represents 0 or 1,

[0076] r represents 0, 1 or 2,

[0077] R 33 Indicates that it can be selected from Group B 2 C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from group D 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from group D 2 C3-C7 cycloalkenyl substituted with one or more substituents, which may be selected from Group E 2 Phenyl substituted with one or more substituents, which may be selected from Group E 2 substituted with one or more substituents in a 6-membered aromatic heterocyclic group, a hydrogen atom or S(O)2R 43 ,

[0078] R 36 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group C1-C3 ...2 Phenyl substituted with one or more substituents, which may be selected from Group E 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a hydrogen atom,

[0079] R 37 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion of the phenyl C1-C3 alkyl group may be selected from Group E 2 substituted with one or more substituents in},

[0080] R 38 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom,

[0081] R 39 Indicates that it can be selected from Group B 2 C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from group D 2 C3-C7 cycloalkyl substituted with one or more substituents, S(O)2R 43 or hydrogen atoms,

[0082] R 40 and R 41 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms,

[0083] R 42 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, which may be selected from Group E 2 phenyl substituted with one or more substituents, or a hydrogen atom,

[0084] R 43 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or may be selected from Group E 2 a phenyl group substituted with one or more substituents,

[0085] R 44 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or an OR 45 NR 46 R 47 or hydrogen atoms,

[0086] R 45 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms,

[0087] R 34 、R 35 、R46 and R 47 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom,

[0088] R 33a and R 34a Together with the nitrogen atoms to which they are bonded, they form a 2 A 3- to 7-membered non-aromatic heterocyclic group substituted with one or more substituents.

[0089] Group D: C3-C6 cycloalkyl which may be substituted with one or more substituents selected from the group consisting of halogen atoms and C1-C3 alkyl groups, C1-C6 alkoxy which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2 ... 2 Phenyl substituted with one or more substituents, which may be selected from the group L 2 a group consisting of a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, a hydroxyl group, a cyano group and a halogen atom.

[0090] Group E: A group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a halogen atom.

[0091] Group F: The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom.

[0092] Group H: The group consisting of C1-C6 alkoxy groups which may be substituted by one or more halogen atoms, C3-C6 alkenyloxy groups which may be substituted by one or more halogen atoms, C3-C6 alkynyloxy groups which may be substituted by one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted by one or more halogen atoms, C3-C6 cycloalkyl groups which may be substituted by one or more halogen atoms, cyano groups, hydroxyl groups and halogen atoms.

[0093] Group J: The group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group.

[0094] Group K: C1-C6 alkyl which may be substituted with one or more halogen atoms, which may be selected from Group J 2 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, OR 49 NR 48 R 49 、C(O)R 49 、C(O)NR 48 R 49 、OC(O)R 48 、OC(O)OR 48 NR 49 C(O)R 48 NR 49 C(O)OR 48 、C(O)OR 49 , a group consisting of halogen atoms, nitro groups, cyano groups and amino groups.

[0095] R 48 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms,

[0096] R 49 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, or a hydrogen atom.

[0097] Group L: C1-C6 alkoxy which may be substituted with one or more halogen atoms, which may be selected from Group J 2 Phenyl substituted with one or more substituents, which may be selected from Group J 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be selected from Group H2 3-7 membered non-aromatic heterocyclic group, amino group, NHR group substituted with one or more substituents 50 NR 50 R 51 , a group consisting of halogen atoms and cyano groups.

[0098] R 50 and R 51 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted with one or more halogen atoms.

[0099] Group M: A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group.

[0100] Group P: A group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group.

[0101] Group T: A group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, and a halogen atom.

[0102] Group U: A group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a sulfanyl group, and a fluorine atom.

[0103] Group V: A group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, a cyano group, and a halogen atom.

[0104] Group X: The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom.

[0105] Group Y: a group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, a cyano group, and a halogen atom.

[0106] Group A 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom.

[0107] Group B 2 : The group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, a cyano group and a halogen atom.

[0108] Group D 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a halogen atom.

[0109] Group E 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom.

[0110] Group F 2 : The group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group.

[0111] Group H 2 : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, and a halogen atom.

[0112] Group J 2 : C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, hydroxyl group, C1-C6 alkoxy group which may be substituted by one or more halogen atoms, C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, sulfanyl group, C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, amino group, NHR group 50 NR 50 R51 、C(O)R 50 、OC(O)R 50 、C(O)OR 50 , cyano, nitro and halogen atoms.

[0113] Group K 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a fluorine atom.

[0114] Group L 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom.

[0115] Group M 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a halogen atom.

[0116] [2] The compound or N-oxide thereof as described in [1], wherein G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a nitrogen atom or CR 3d .

[0117] [3] The compound or N-oxide thereof as described in [1], wherein G 1 CR 3a , G 2 CR 3b , G3 CR 3c , G 4 CR 3d .

[0118] [4] The compound according to any one of [1] to [3] or its N-oxide, wherein Q is Q 1 , in Q 1 In, Z 1 、X 1 、X 2 and X 3 The combination is:

[0119] Z 1 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g combination of;

[0120] Z 1 is an oxygen atom, X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g combination of;

[0121] Z 1 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 3 is a combination of nitrogen atoms;

[0122] Z 1 is a sulfur atom, X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g combination of;

[0123] Z 1 is a sulfur atom, X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g combination of;

[0124] Z 1 NR 3j , X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g combination of;

[0125] Z 1 NR 3j , X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g or, Z 1 NR 3j , X 1 CR 3e , X 2 CR 3f , X 3 A combination of nitrogen atoms.

[0126] [5] The compound or N-oxide thereof according to any one of [1] to [3], wherein Q is Q 2 , in Q 2 In, Z 2 、X 1 、X 2 and X 4 The combination is:

[0127] Z 2 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f , X 4 CR 3h combination of;

[0128] Z 2 is an oxygen atom, X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h combination of;

[0129] Z 2 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 4 is a combination of nitrogen atoms;

[0130] Z 2 NR 3k , X 1 is a nitrogen atom, X 2 CR 3f , X 4 CR 3h combination of;

[0131] Z 2 NR 3k , X1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h combination of;

[0132] Z 2 NR 3k , X 1 CR 3e , X 2 CR 3f , X 4 is a combination of nitrogen atoms;

[0133] Z 2 NR 3k , X 1 CR 3e , X 2 CR 3f , X 4 CR 3h or, Z 2 NR 3k , X 1 is a nitrogen atom, X 2 is a nitrogen atom, X 4 CR 3h combination.

[0134] [6] The compound or N-oxide thereof according to any one of [1] to [5], wherein R 2 For ethyl.

[0135] [7] The compound according to any one of [1] to [6] or its N-oxide, wherein W is an oxygen atom.

[0136] [8] A harmful arthropod control composition comprising the compound or its N-oxide according to any one of [1] to [7].

[0137] [9] A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound or N-oxide thereof according to any one of [1] to [7],

[0138] Group (a): a group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients;

[0139] Group (b): bactericidal active ingredients;

[0140] Group (c): plant growth regulating ingredients;

[0141] Group (d): repellent ingredients.

[0142]

[10] A method for controlling harmful arthropods, comprising applying an effective amount of the compound or N-oxide thereof according to any one of [1] to [7] or an effective amount of the composition according to [9] to the harmful arthropods or to a habitat of the harmful arthropods.

[0143]

[11] Seeds or vegetative propagation organs containing an effective amount of the compound or N-oxide thereof according to any one of [1] to [7] or an effective amount of the composition according to [9].

[0144]

[12] A compound represented by formula (II) or a salt thereof (hereinafter, the compound represented by formula (II) or a salt thereof is referred to as intermediate A).

[0145] [Chemical Formula 3]

[0146]

[0147] [In the formula, the symbols have the same meanings as [1].]

[0148] Effects of the Invention

[0149] According to the present invention, harmful arthropods can be controlled. DETAILED DESCRIPTION

[0150] The substituents in the present invention are explained.

[0151] The halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0152] When the substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different.

[0153] In this specification, the expression "CX-CY" means that the number of carbon atoms is X to Y. For example, the expression "C1-C6" means that the number of carbon atoms is 1 to 6.

[0154] The chain hydrocarbon group refers to an alkyl group, an alkenyl group or an alkynyl group.

[0155] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0156] Examples of the alkenyl group include ethenyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl.

[0157] Examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl.

[0158] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.

[0159] Examples of the alkenyloxy group include a 2-propenyloxy group, a 2-butenyloxy group, and a 5-hexenyloxy group.

[0160] Examples of the alkynyloxy group include a 2-propynyloxy group, a 2-butynyloxy group, and a 5-hexynyloxy group.

[0161] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0162] Examples of the cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0163] The 3- to 7-membered non-aromatic heterocyclic group represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazepane ring, a thiomorpholine ring or a 1,4-thiazepane ring.

[0164] A 3-7 membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from Group P, a 3-7 membered non-aromatic heterocyclic group which may be selected from Group F 2 3-7 membered non-aromatic heterocyclic group substituted with one or more substituents, or may be selected from Group H 2 Examples of the 3- to 7-membered non-aromatic heterocyclic group substituted with one or more substituents in include the following groups.

[0165] [Chemical Formula 4]

[0166]

[0167] The term "5- or 6-membered aromatic heterocyclic group" refers to a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group. The term "5-membered aromatic heterocyclic group" refers to a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group. The term "6-membered aromatic heterocyclic group" refers to a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group.

[0168] The 5- or 6-membered heterocyclic group refers to a 5- or 6-membered aromatic heterocyclic group or a 5- or 6-membered non-aromatic heterocyclic group, and examples thereof include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, piperidinyl, tetrahydropyrimidinyl, hexahydropyrimidinyl, piperazinyl, oxazolidinyl, isoxazolidinyl, 1,3-oxazinyl, morpholinyl, thiazolidinyl, isothiazolidinyl, 1,3-thiazolyl and thiomorpholinyl.

[0169] Examples of the (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms include cyclopropylmethyl, (2-fluorocyclopropyl)methyl, cyclopropyl(fluoro)methyl, and (2-fluorocyclopropyl)(fluoro)methyl.

[0170] As the phenyl C1-C3 alkyl group, the phenyl portion of the phenyl C1-C3 alkyl group may be selected from the group consisting of 2 substituted with one or more substituents in}, or phenyl C1-C3 alkyl {the phenyl portion in the phenyl C1-C3 alkyl may be selected from Group E 2 The group consisting of 1 or more substituents in the group {is substituted with} includes, for example, benzyl, 2-fluorobenzyl, 4-chlorobenzyl, 4-(trifluoromethyl)benzyl and 2-[4-(trifluoromethyl)phenyl]ethyl.

[0171] Examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group.

[0172] Examples of the alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group.

[0173] Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.

[0174] Examples of the alkylamino group include a methylamino group, an ethylamino group, an isopropylamino group, and a hexylamino group.

[0175] Examples of the dialkylamino group include a dimethylamino group, an ethylmethylamino group, an isopropylmethylamino group, and a dihexylamino group.

[0176] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, a 2-methylpropionyl group, and a hexanoyl group.

[0177] Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, and a pentyloxycarbonyl group.

[0178] Examples of the N-oxide of the compound represented by formula (I) include compounds represented by the following formula.

[0179] [Chemical Formula 5]

[0180]

[0181] [In the formula, the symbols have the same meanings as above.]

[0182] The compounds of the present invention and intermediate A may exist in one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, and geometric isomers. The compounds of the present invention and intermediate A include individual stereoisomers and mixtures of stereoisomers in any ratio.

[0183] The compounds of the present invention and the compounds represented by formula (II) may form acid addition salts. Examples of acids that form acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. Acid addition salts can be obtained by mixing the compounds of the present invention or the compounds represented by formula (II) with an acid.

[0184] As an embodiment of the compound N of the present invention, the following compounds can be mentioned.

[0185] [Embodiment 1] In the compound N of the present invention, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0186] [Embodiment 2] In the compound N of the present invention, R 1 A compound which is a C1-C6 alkyl group.

[0187] [Embodiment 3] In the compound N of the present invention, R 1 A compound containing methyl.

[0188] [Embodiment 4] In the compound N of the present invention, R 2 A compound which is a C1-C6 alkyl group.

[0189] [Embodiment 5] In the compound N of the present invention, R 2 An ethyl compound.

[0190] [Embodiment 6] In the compound N of the present invention, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0191] [Embodiment 7] In the compound N of the present invention, R 2 NR6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0192] [Embodiment 8] A compound wherein W in the compound N of the present invention is an oxygen atom.

[0193] [Embodiment 9] In the compound N of the present invention, G 1 , G 2 , G 3 and G 4 The combination is: G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a combination of nitrogen atoms; G 1 CR 3a , G 2 CR 3b , G 3 is a nitrogen atom, G 4 CR 3d Combination of G 1 CR 3a , G 2 is a nitrogen atom, G 3 CR 3c , G 4 CR 3d Combination of G 1 is a nitrogen atom, G 2 CR 3b , G 3 CR 3c , G 4 CR 3d or G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d Combination of R 3a 、R 3c and R 3d is a hydrogen atom, R 3bIt is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a phenyl group which may be substituted by one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more halogen atoms, or a compound containing a halogen atom.

[0194] [Embodiment 10] In the compound N of the present invention, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a nitrogen atom or CR 3d , R 3a 、R 3c and R 3d is a hydrogen atom, R 3b It is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a compound containing a halogen atom.

[0195] [Embodiment 11] In the compound N of the present invention, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d , R 3a 、R 3c and R 3d is a hydrogen atom, R 3b It is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a compound containing a halogen atom.

[0196] [Embodiment 12] In the compound N of the present invention, G 1 , G 2 , G 3 and G 4 The combination is: G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a combination of nitrogen atoms; G 1 CR 3a , G 2 CR 3b , G 3 is a nitrogen atom, G 4 CR 3d Combination of G 1 CR 3a , G2 is a nitrogen atom, G 3 CR 3c , G 4 CR 3d Combination of G 1 is a nitrogen atom, G 2 CR 3b , G 3 CR 3c , G 4 CR 3d or G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d Combination of R 3a 、R 3b and R 3d is a hydrogen atom, R 3c A compound containing a halogen atom.

[0197] [Embodiment 13] In the compound N of the present invention, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a nitrogen atom or CR 3d , R 3a 、R 3b and R 3d is a hydrogen atom, R 3c A compound containing a halogen atom.

[0198] [Embodiment 14] In the compound N of the present invention, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d , R 3a 、R 3b and R 3d is a hydrogen atom, R 3c A compound containing a halogen atom.

[0199] [Method 15] In Method 4, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0200] [Method 16] In Method 5, R1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0201] [Method 17] In Method 6, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0202] [Method 18] In Method 7, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0203] [Method 19] In Method 8, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0204] [Method 20] In method 9, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0205] [Method 21] In method 10, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0206] [Method 22] In method 11, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0207] [Method 23] In method 12, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0208] [Method 24] In method 13, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0209] [Method 25] In method 14, R 1 A compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group D.

[0210] [Method 26] In Method 4, R 1 A compound which is a C1-C6 alkyl group.

[0211] [Method 27] In Method 5, R 1 A compound which is a C1-C6 alkyl group.

[0212] [Method 28] In Method 6, R 1 A compound which is a C1-C6 alkyl group.

[0213] [Method 29] In Method 7, R 1 A compound which is a C1-C6 alkyl group.

[0214] [Method 30] In method 8, R 1 A compound which is a C1-C6 alkyl group.

[0215] [Method 31] In Method 9, R 1 A compound which is a C1-C6 alkyl group.

[0216] [Method 32] In method 10, R 1 A compound which is a C1-C6 alkyl group.

[0217] [Method 33] In method 11, R 1 A compound which is a C1-C6 alkyl group.

[0218] [Method 34] In method 12, R 1 A compound which is a C1-C6 alkyl group.

[0219] [Method 35] In method 13, R 1 A compound which is a C1-C6 alkyl group.

[0220] [Method 36] In method 14, R 1 A compound which is a C1-C6 alkyl group.

[0221] [Method 37] In Method 4, R 1 A compound containing methyl.

[0222] [Method 38] In Method 5, R 1 A compound containing methyl.

[0223] [Method 39] In Method 6, R 1 A compound containing methyl.

[0224] [Method 40] In Method 7, R 1 A compound containing methyl.

[0225] [Method 41] In Method 8, R 1 A compound containing methyl.

[0226] [Method 42] In method 9, R 1 A compound containing methyl.

[0227] [Method 43] In method 10, R 1 A compound containing methyl.

[0228] [Method 44] In method 11, R 1 A compound containing methyl.

[0229] [Method 45] In method 12, R 1 A compound containing methyl.

[0230] [Method 46] In method 13, R 1 A compound containing methyl.

[0231] [Method 47] In method 14, R 1 A compound containing methyl.

[0232] [Method 48] In method 8, R 2 A compound which is a C1-C6 alkyl group.

[0233] [Method 49] In method 9, R 2 A compound which is a C1-C6 alkyl group.

[0234] [Method 50] In method 10, R 2 A compound which is a C1-C6 alkyl group.

[0235] [Method 51] In method 11, R 2 A compound which is a C1-C6 alkyl group.

[0236] [Method 52] In method 12, R 2 A compound which is a C1-C6 alkyl group.

[0237] [Method 53] In method 13, R 2 A compound which is a C1-C6 alkyl group.

[0238] [Method 54] In method 14, R 2 A compound which is a C1-C6 alkyl group.

[0239] [Method 55] In method 8, R 2 An ethyl compound.

[0240] [Method 56] In method 9, R 2 An ethyl compound.

[0241] [Method 57] In method 10, R 2 An ethyl compound.

[0242] [Method 58] In method 11, R 2 An ethyl compound.

[0243] [Method 59] In method 12, R 2 An ethyl compound.

[0244] [Method 60] In method 13, R 2 An ethyl compound.

[0245] [Method 61] In method 14, R 2 An ethyl compound.

[0246] [Method 62] In method 8, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0247] [Method 63] In method 9, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0248] [Method 64] In method 10, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0249] [Method 65] In method 11, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0250] [Method 66] In method 12, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0251] [Method 67] In method 13, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0252] [Method 68] In method 14, R 2 NR 6 R 7 , R 6 and R 7Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0253] [Method 69] In Method 8, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0254] [Method 70] In method 9, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0255] [Method 71] In method 10, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0256] [Method 72] In method 11, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0257] [Method 73] In method 12, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0258] [Method 74] In method 13, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0259] [Method 75] In method 14, R 2 NR 6 R7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0260] [Embodiment 76] In Embodiment 9, a compound wherein W is an oxygen atom.

[0261] [Embodiment 77] In Embodiment 10, a compound wherein W is an oxygen atom.

[0262] [Embodiment 78] In Embodiment 11, a compound wherein W is an oxygen atom.

[0263] [Embodiment 79] In Embodiment 12, a compound wherein W is an oxygen atom.

[0264] [Embodiment 80] In Embodiment 13, a compound wherein W is an oxygen atom.

[0265] [Embodiment 81] A compound in Embodiment 14, wherein W is an oxygen atom.

[0266] [Embodiment 82] In the compound N of the present invention, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0267] [Embodiment 83] In the compound N of the present invention, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0268] [Embodiment 84] In the compound N of the present invention, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0269] [Embodiment 85] In the compound N of the present invention, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0270] [Embodiment 86] In the compound N of the present invention, R 1 is methyl, R 2 An ethyl compound.

[0271] [Embodiment 87] In the compound N of the present invention, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0272] [Embodiment 88] In the compound N of the present invention, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0273] [Embodiment 89] In the compound N of the present invention, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0274] [Embodiment 90] In the compound N of the present invention, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0275] [Embodiment 91] In the compound N of the present invention, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0276] [Embodiment 92] In the compound N of the present invention, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0277] [Embodiment 93] In the compound N of the present invention, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0278] [Method 94] In Method 8, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0279] [Method 95] In method 9, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0280] [Method 96] In method 10, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0281] [Method 97] In method 11, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0282] [Method 98] In method 12, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0283] [Method 99] In method 13, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0284] [Method 100] In method 14, R 1 is a C1-C6 alkyl group, R 2 An ethyl compound.

[0285] [Method 101] In Method 4, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0286] [Method 102] In Method 5, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0287] [Method 103] In Method 6, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0288] [Method 104] In Method 7, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0289] [Method 105] In method 9, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0290] [Method 106] In method 10, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0291] [Method 107] In method 11, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0292] [Method 108] In method 12, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0293] [Method 109] In method 13, R1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0294] [Method 110] In method 14, R 1 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0295] [Method 111] In Method 8, R 1 is methyl, R 2 An ethyl compound.

[0296] [Method 112] In method 9, R 1 is methyl, R 2 An ethyl compound.

[0297] [Method 113] In method 10, R 1 is methyl, R 2 An ethyl compound.

[0298] [Method 114] In method 11, R 1 is methyl, R 2 An ethyl compound.

[0299] [Method 115] In method 12, R 1 is methyl, R 2 An ethyl compound.

[0300] [Method 116] In Method 13, R 1 is methyl, R 2 An ethyl compound.

[0301] [Method 117] In method 14, R 1 is methyl, R 2 An ethyl compound.

[0302] [Method 118] In Method 4, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0303] [Method 119] In Method 5, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0304] [Method 120] In Method 6, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0305] [Method 121] In Method 7, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0306] [Method 122] In method 9, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0307] [Method 123] In method 10, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0308] [Method 124] In method 11, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0309] [Method 125] In method 12, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0310] [Method 126] In Method 13, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0311] [Method 127] In Method 14, R 1 A compound in which R is a methyl group and W is an oxygen atom.

[0312] [Method 128] In Method 1, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0313] [Method 129] In Method 2, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0314] [Method 130] In Method 3, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0315] [Method 131] In Method 9, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0316] [Method 132] In method 10, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0317] [Method 133] In Method 11, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0318] [Method 134] In method 12, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0319] [Method 135] In Method 13, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0320] [Method 136] In Method 14, R 2 A compound wherein R is a C1-C6 alkyl group and W is an oxygen atom.

[0321] [Method 137] In Method 1, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0322] [Method 138] In Method 2, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0323] [Method 139] In Method 3, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0324] [Method 140] In Method 9, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0325] [Method 141] In method 10, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0326] [Method 142] In method 11, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0327] [Method 143] In Method 12, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0328] [Method 144] In Method 13, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0329] [Method 145] In Method 14, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0330] [Method 146] In Method 8, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0331] [Method 147] In Method 9, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0332] [Method 148] In method 10, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7, R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0333] [Method 149] In Method 11, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0334] [Method 150] In method 12, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0335] [Method 151] In Method 13, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0336] [Method 152] In method 14, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0337] [Method 153] In Method 8, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0338] [Method 154] In Method 9, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0339] [Method 155] In method 10, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0340] [Method 156] In method 11, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0341] [Method 157] In Method 12, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0342] [Method 158] In Method 13, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0343] [Method 159] In Method 14, R 1 is a C1-C6 alkyl group, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0344] [Method 160] In Method 8, R 1 is methyl, R 2 NR6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0345] [Method 161] In Method 9, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0346] [Method 162] In method 10, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0347] [Method 163] In Method 11, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0348] [Method 164] In method 12, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0349] [Method 165] In Method 13, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0350] [Method 166] In Method 14, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0351] [Method 167] In Method 8, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0352] [Method 168] In Method 9, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0353] [Method 169] In method 10, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0354] [Method 170] In Method 11, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0355] [Method 171] In method 12, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0356] [Method 172] In Method 13, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0357] [Method 173] In Method 14, R 1 is methyl, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0358] [Method 174] In Method 1, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0359] [Method 175] In Method 2, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0360] [Method 176] In Method 3, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0361] [Method 177] In Method 9, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0362] [Method 178] In method 10, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0363] [Method 179] In Method 11, R 2 NR6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0364] [Method 180] In Method 12, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0365] [Method 181] In Method 13, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0366] [Method 182] In Method 14, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0367] [Method 183] In Method 1, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0368] [Method 184] In Method 2, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0369] [Method 185] In Method 3, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0370] [Method 186] In Method 9, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0371] [Method 187] In method 10, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0372] [Method 188] In Method 11, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0373] [Method 189] In Method 12, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0374] [Method 190] In Method 13, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0375] [Method 191] In Method 14, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0376] [Embodiment 192] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1, Z 1 、X 1 、X 2 and X 3 The combination is: Z 1 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f 、X 3 CR 3g Combination of Z 1 is an oxygen atom, X 1 CR 3e 、X 2 is a nitrogen atom, X 3 CR 3g Combination of Z 1 is an oxygen atom, X 1 CR 3e 、X 2 CR 3f 、X 3 is a combination of nitrogen atoms; Z 1 is an oxygen atom, X 1 CR 3e 、X 2 CR 3f 、X 3 CR 3g Combination of Z 1 NR 3j 、X 1 is a nitrogen atom, X 2 CR 3f 、X 3 CR 3g Combination of Z 1 NR 3j 、X 1 CR 3e 、X 2 is a nitrogen atom, X 3 CR 3g or, Z 1 NR 3j 、X 1 CR 3e 、X 2 CR 3f 、X 3 is a combination of nitrogen atoms, R 3e is a hydrogen atom, R 3f and R 3g are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, hydrogen atoms or halogen atoms, R 3jThe compound is a methyl group which may be substituted by one or more halogen atoms, a C2-C4 alkyl group which may be substituted by one or more fluorine atoms, a C5-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0377] [Embodiment 193] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 、X 1 、X 2 and X 4 The combination is: Z 2 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f 、X 4 CR 3h combination; Z is an oxygen atom, X 1 CR 3e 、X 2 is a nitrogen atom, X 4 CR 3h Combination of Z 2 is an oxygen atom, X 1 CR 3e 、X 2 CR 3f 、X 4 is a combination of nitrogen atoms; Z 2 NR 3k 、X 1 is a nitrogen atom, X 2 CR 3f 、X 4 CR 3h Combination of Z 2 NR 3k 、X 1 CR 3e 、X 2 is a nitrogen atom, X 4 CR 3h Combination of Z 2 NR 3k 、X 1 CR 3e 、X 2 CR 3f 、X 4 is a combination of nitrogen atoms; or, Z is NR 3k 、X 1 CR 3e 、X 2 CR 3f 、X 4 CR 3h Combination of R 3e and R3h are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, or hydrogen atoms, R 3f is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, OR 33 , hydrogen atom or halogen atom, R 3k A compound which is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0378] [Embodiment 194] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1 , Z 1 、X 1 、X 2 and X 3 The combination is: Z 1 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f 、X 3 CR 3g Combination of Z 1 is an oxygen atom, X 1 CR 3e 、X 2 is a nitrogen atom, X 3 CR 3g Combination of Z 1 is an oxygen atom, X 1 CR 3e 、X 2 CR 3f 、X 3 is a combination of nitrogen atoms; or, Z 1 is an oxygen atom, X 1 CR 3e 、X 2 CR 3f 、X 3 CR 3g Combination of R 3e is a hydrogen atom, R 3f and R 3g Compounds which are the same or different from each other and are C1-C6 alkyl groups, hydrogen atoms or halogen atoms which may be substituted with one or more halogen atoms.

[0379] [Embodiment 195] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1 , Z 1 、X 1 、X 2 and X 3 The combination is: Z 1 NR 3j 、X1 is a nitrogen atom, X 2 CR 3f 、X 3 CR 3g Combination of Z 1 NR 3j 、X 1 CR 3e 、X 2 is a nitrogen atom, X 3 CR 3g or, Z 1 NR 3j 、X 1 CR 3e 、X 2 CR 3f 、X 3 is a combination of nitrogen atoms, R 3e is a hydrogen atom, R 3f and R 3g are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, hydrogen atoms or halogen atoms, R 3j A compound which is a methyl group which may be substituted by one or more halogen atoms, a C2-C4 alkyl group which may be substituted by one or more fluorine atoms, a C5-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0380] [Embodiment 196] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 、X 1 、X 2 and X 4 The combination is: Z 2 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f 、X 4 CR 3h Combination of Z 2 is an oxygen atom, X 1 CR 3e 、X 2 is a nitrogen atom, X 4 CR 3h or, Z 2 is an oxygen atom, X 1 CR 3e 、X 2 CR 3f 、X 4 is a combination of nitrogen atoms, R 3e and R 3hare the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, or hydrogen atoms, R 3f Compounds which are the same or different from each other and are C1-C6 alkyl groups, hydrogen atoms or halogen atoms which may be substituted with one or more halogen atoms.

[0381] [Embodiment 197] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 、X 1 、X 2 and X 4 The combination is: Z 2 NR 3k 、X 1 is a nitrogen atom, X 2 CR 3f 、X 4 CR 3h Combination of Z 2 NR 3k 、X 1 CR 3e 、X 2 is a nitrogen atom, X 4 CR 3h Combination of Z 2 NR 3k 、X 1 CR 3e 、X 2 CR 3f 、X 4 is a combination of nitrogen atoms; or, Z 2 NR 3k 、X 1 CR 3e 、X 2 CR 3f 、X 4 CR 3h Combination of R 3e and R 3h are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, or hydrogen atoms, R 3f is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, OR 33 , hydrogen atoms or halogen atoms.

[0382] [Embodiment 198] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 、X 1 、X 2 and X 4 The combination is: Z 2 NR3k 、X 1 is a nitrogen atom, X 2 CR 3f 、X 4 CR 3h Combination of Z 2 NR 3k 、X 1 CR 3e 、X 2 is a nitrogen atom, X 4 CR 3h or, Z 2 NR 3k 、X 1 CR 3e 、X 2 CR 3f 、X 4 is a combination of nitrogen atoms; or, Z 2 NR 3k 、X 1 CR 3e 、X 2 CR 3f 、X 4 CR 3h Combination of R 3e and R 3h are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, or hydrogen atoms, R 3f A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0383] [Embodiment 199] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1 , Z 1 NR 3j , X 1 CR 3e , X 2 CR 3f , X 3 is a nitrogen atom, R 3e is a hydrogen atom, R 3f is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom, R 3j A compound which is a methyl group which may be substituted by one or more halogen atoms, a C2-C4 alkyl group which may be substituted by one or more fluorine atoms, a C5-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0384] [Embodiment 200] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1 , Z1 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 3 is a nitrogen atom, R 3e is a hydrogen atom, R 3f A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0385] [Embodiment 201] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1 , Z is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 3 CR 3g , R 3e and R 3f is a hydrogen atom, R 3g A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0386] [Embodiment 202] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 NR 3k , X 1 CR 3e , X 2 CR 3f , X 4 is a nitrogen atom, R 3e is a hydrogen atom, R 3f is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom, R 3k A compound which is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0387] [Embodiment 203] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z is NR 3j , X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h , R 3e and R 3h is a hydrogen atom, R 3jA compound which is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0388] [Embodiment 204] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 is an oxygen atom, X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h , R 3e and R 3h Compounds which are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, or hydrogen atoms.

[0389] [Embodiment 205] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 2 , Z 2 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 4 is a nitrogen atom, R 3e is a hydrogen atom, R 3f A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0390] [Embodiment 206] In any one of Embodiments 1 to 191 or Compound N of the present invention, Q is Q 1 , Z 1 is a sulfur atom, X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g , R 3e is a hydrogen atom, R 3g A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0391] [Embodiment 207] In Embodiments 1 to 191 or the compound N of the present invention, Q is Q 1 , Z 1 is a sulfur atom, X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g , R 3e is a hydrogen atom, R 3gA compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0392] As embodiments of the compound represented by formula (II) (hereinafter also referred to as intermediate C), the following compounds can be mentioned.

[0393] [Form C1] In the intermediate C, R 2 A compound which is a C1-C6 alkyl group.

[0394] [Form C2] In intermediate C, R 2 An ethyl compound.

[0395] [Form C3] In the intermediate C, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0396] [Form C4] In the intermediate C, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0397] [Embodiment C5] A compound wherein W in the intermediate C is an oxygen atom.

[0398] [Form C6] In the intermediate C, G 1 , G 2 , G 3 and G 4 The combination is: G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a combination of nitrogen atoms; G 1 CR 3a , G 2 CR 3b , G 3 is a nitrogen atom, G 4 CR 3d Combination of G 1 CR 3a , G 2 is a nitrogen atom, G 3 CR 3c , G 4 CR3d Combination of G 1 is a nitrogen atom, G 2 CR 3b , G 3 CR 3c , G 4 CR 3d or G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d Combination of R 3a 、R 3c and R 3d is a hydrogen atom, R 3b It is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a phenyl group which may be substituted by one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more halogen atoms, or a compound containing a halogen atom.

[0399] [Form C7] In the intermediate C, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a nitrogen atom or CR 3d , R 3a 、R 3c and R 3d is a hydrogen atom, R 3b It is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a compound containing a halogen atom.

[0400] [Form C8] In the intermediate C, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d , R 3a 、R 3c and R 3d is a hydrogen atom, R 3b It is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a compound containing a halogen atom.

[0401] [Form C9] In the intermediate C, G 1, G 2 , G 3 and G 4 The combination is: G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a combination of nitrogen atoms; G 1 CR 3a , G 2 CR 3b , G 3 is a nitrogen atom, G 4 CR 3d Combination of G 1 CR 3a , G 2 is a nitrogen atom, G 3 CR 3c , G 4 CR 3d Combination of G 1 is a nitrogen atom, G 2 CR 3b , G 3 CR 3c , G 4 CR 3d or G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d Combination of R 3a 、R 3b and R 3d is a hydrogen atom, R 3c A compound containing a halogen atom.

[0402] [Form C10] In the intermediate C, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a nitrogen atom or CR 3d , R 3a 、R 3b and R 3d is a hydrogen atom, R 3c A compound containing a halogen atom.

[0403] [Form C11] In the intermediate C, G1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d , R 3a 、R 3b and R 3d is a hydrogen atom, R 3c A compound containing a halogen atom.

[0404] [Embodiment C12] A compound wherein n is 0 in the intermediate C.

[0405] [Form C13] The compound in Form C1, wherein n is 0.

[0406] [Form C14] The compound in Form C2, wherein n is 0.

[0407] [Form C15] The compound in Form C3, wherein n is 0.

[0408] [Form C16] The compound in Form C4, wherein n is 0.

[0409] [Form C17] The compound in Form C5, wherein n is 0.

[0410] [Form C18] The compound in Form C6, wherein n is 0.

[0411] [Form C19] The compound in Form C7, wherein n is 0.

[0412] [Form C20] The compound in Form C8, wherein n is 0.

[0413] [Form C21] The compound in Form C9, wherein n is 0.

[0414] [Form C22] The compound in Form C10, wherein n is 0.

[0415] [Form C23] The compound in Form C11, wherein n is 0.

[0416] [Method C24] In method C5, R 2 A compound which is a C1-C6 alkyl group.

[0417] [Method C25] In Method C6, R 2 A compound which is a C1-C6 alkyl group.

[0418] [Method C26] In Method C7, R 2 A compound which is a C1-C6 alkyl group.

[0419] [Method C27] In method C8, R2 A compound which is a C1-C6 alkyl group.

[0420] [Method C28] In method C9, R 2 A compound which is a C1-C6 alkyl group.

[0421] [Method C29] In Method C10, R 2 A compound which is a C1-C6 alkyl group.

[0422] [Method C30] In Method C11, R 2 A compound which is a C1-C6 alkyl group.

[0423] [Method C31] In Method C5, R 2 An ethyl compound.

[0424] [Method C32] In Method C6, R 2 An ethyl compound.

[0425] [Method C33] In Method C7, R 2 An ethyl compound.

[0426] [Method C34] In method C8, R 2 An ethyl compound.

[0427] [Method C35] In Method C9, R 2 An ethyl compound.

[0428] [Method C36] In Method C10, R 2 An ethyl compound.

[0429] [Method C37] In Method C11, R 2 An ethyl compound.

[0430] [Method C38] In Method C5, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0431] [Method C39] In Method C6, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0432] [Method C40] In Method C7, R 2 NR 6 R7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0433] [Method C41] In method C8, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0434] [Method C42] In method C9, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0435] [Method C43] In Method C10, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0436] [Method C44] In Method C11, R 2 NR 6 R 7 , R 6 and R 7 Compounds which are the same or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0437] [Method C45] In method C5, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0438] [Method C46] In method C6, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0439] [Method C47] In method C7, R 2 NR 6 R7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0440] [Method C48] In method C8, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0441] [Method C49] In method C9, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0442] [Method C50] In method C10, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0443] [Method C51] In Method C11, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bound, they form compounds that are aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl.

[0444] [Embodiment C52] A compound in Embodiment C6, wherein W is an oxygen atom.

[0445] [Embodiment C53] The compound in Embodiment C7, wherein W is an oxygen atom.

[0446] [Embodiment C54] A compound in Embodiment C8, wherein W is an oxygen atom.

[0447] [Embodiment C55] A compound in Embodiment C9, wherein W is an oxygen atom.

[0448] [Embodiment C56] The compound in Embodiment C10, wherein W is an oxygen atom.

[0449] [Embodiment C57] In Embodiment C11, the compound wherein W is an oxygen atom.

[0450] [Method C58] In Method C6, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0451] [Method C59] In Method C7, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0452] [Method C60] In Method C8, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0453] [Method C61] In Method C9, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0454] [Method C62] In method C10, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0455] [Method C63] In Method C11, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0456] [Method C64] In Method C12, R 2 A compound in which R is an ethyl group and W is an oxygen atom.

[0457] [Method C65] In method C6, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0458] [Method C66] In Method C7, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0459] [Method C67] In method C8, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0460] [Method C68] In Method C9, R 2 NR 6 R 7 , R 6 and R7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0461] [Method C69] In Method C10, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0462] [Method C70] In Method C11, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0463] [Method C71] In Method C12, R 2 NR 6 R 7 , R 6 and R 7 The compound is the same or different from each other and is a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom.

[0464] [Method C72] In Method C6, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0465] [Method C73] In method C7, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0466] [Method C74] In Method C8, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0467] [Method C75] In Method C9, R2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0468] [Method C76] In Method C10, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0469] [Method C77] In Method C11, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0470] [Method C78] In Method C12, R 2 NR 6 R 7 , R 6 and R 7 Together with the nitrogen atom to which they are bonded, they form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, and W is an oxygen atom.

[0471] [Method C79] In Method C5, R 2 The compound wherein is ethyl and n is 0.

[0472] [Mode C80] In Mode C6, R 2 The compound wherein is ethyl and n is 0.

[0473] [Method C81] In Method C7, R 2 The compound wherein is ethyl and n is 0.

[0474] [Method C82] In method C8, R 2 The compound wherein is ethyl and n is 0.

[0475] [Method C83] In Method C9, R 2 The compound wherein is ethyl and n is 0.

[0476] [Method C84] In method C10, R 2 The compound wherein is ethyl and n is 0.

[0477] [Method C85] In Method C11, R 2 The compound wherein is ethyl and n is 0.

[0478] [Form C86] The compound in Form C1, wherein W is an oxygen atom and n is 0.

[0479] [Form C87] The compound in Form C2, wherein W is an oxygen atom and n is 0.

[0480] [Form C88] The compound in Form C3, wherein W is an oxygen atom and n is 0.

[0481] [Form C89] The compound in Form C4, wherein W is an oxygen atom and n is 0.

[0482] [Embodiment C90] The compound in Embodiment C6, wherein W is an oxygen atom and n is 0.

[0483] [Embodiment C91] The compound in Embodiment C7, wherein W is an oxygen atom and n is 0.

[0484] [Form C92] The compound in Form C8, wherein W is an oxygen atom and n is 0.

[0485] [Embodiment C93] The compound in Embodiment C9, wherein W is an oxygen atom and n is 0.

[0486] [Embodiment C94] The compound in Embodiment C10, wherein W is an oxygen atom and n is 0.

[0487] [Embodiment C95] The compound in Embodiment C11, wherein W is an oxygen atom and n is 0.

[0488] [Embodiment C96] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 1 , Z 1 NR 3j , X 1 CR 3e , X 2 CR 3f , X 3 is a nitrogen atom, R 3e is a hydrogen atom, R 3f is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom, R 3j A compound which is a methyl group which may be substituted by one or more halogen atoms, a C2-C4 alkyl group which may be substituted by one or more fluorine atoms, a C5-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0489] [Embodiment C97] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 1, Z 1 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 3 is a nitrogen atom, R 3e is a hydrogen atom, R 3f A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0490] [Embodiment C98] In any of Embodiments C1 to C95 or Intermediate C, Q is Q 1 , Z 1 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 3 CR 3g , R 3e and R 3f is a hydrogen atom, R 3g A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0491] [Embodiment C99] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 2 , Z 2 NR 3k , X 1 CR 3e , X 2 CR 3f , X 4 is a nitrogen atom, R 3e is a hydrogen atom, R 3f is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom, R 3k A compound which is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0492] [Embodiment C100] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 2 , Z is NR 3j , X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h , R 3e and R 3h is a hydrogen atom, R 3jA compound which is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms.

[0493] [Embodiment C101] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 2 , Z 2 is an oxygen atom, X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h , R 3e and R 3h Compounds which are the same or different and are C1-C6 alkyl groups which may be substituted with one or more halogen atoms, or hydrogen atoms.

[0494] [Embodiment C102] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 2 , Z 2 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 4 is a nitrogen atom, R 3e is a hydrogen atom, R 3f A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0495] [Embodiment C103] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 1 , Z 1 is a sulfur atom, X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g , R 3e is a hydrogen atom, R 3g A compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0496] [Embodiment C104] In any one of Embodiments C1 to C95 or Intermediate C, Q is Q 1 , Z 1 is a sulfur atom, X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g , R 3e is a hydrogen atom, R 3gA compound which is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a hydrogen atom or a halogen atom.

[0497] Next, the method for producing the compound of the present invention will be described.

[0498] Manufacturing method 1

[0499] The compound represented by formula (Ib) (hereinafter referred to as compound (Ib)) or the compound represented by formula (Ic) (hereinafter referred to as compound (Ic)) can be produced by reacting the compound represented by formula (Ia) (hereinafter referred to as compound (Ia)) with an oxidizing agent.

[0500] [Chemical Formula 6]

[0501]

[0502] [In the formula, the symbols have the same meanings as above.]

[0503] First, a method for producing compound (Ib) from compound (Ia) will be described.

[0504] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more thereof.

[0505] Examples of the oxidizing agent used in the reaction include sodium periodate, meta-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.

[0506] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be added as needed.

[0507] As the base used in the reaction, sodium carbonate can be mentioned. When a base is used in the reaction, it is usually used in a ratio of 0.01 to 1 mol based on 1 mol of Compound (Ia).

[0508] Examples of the catalyst used in the reaction include tungstic acid and sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used in a ratio of 0.01 to 0.5 mol per 1 mol of Compound (Ia).

[0509] In the reaction, the oxidizing agent is usually used in a ratio of 1 to 1.2 mol based on 1 mol of Compound (Ia).

[0510] The reaction temperature is usually within the range of -20 to 80° C. The reaction time is usually within the range of 0.1 to 12 hours.

[0511] After the reaction is completed, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of an alkali (e.g., sodium bicarbonate) as needed. The organic layer is dried and concentrated to obtain compound (Ib).

[0512] Next, a method for producing compound (Ic) from compound (Ib) will be described.

[0513] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more thereof.

[0514] Examples of the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide.

[0515] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be added as needed.

[0516] As the base used in the reaction, sodium carbonate can be mentioned. When a base is used in the reaction, it is usually used in a ratio of 0.01 to 1 mol based on 1 mol of compound (Ib).

[0517] Examples of the catalyst used in the reaction include sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used in a ratio of 0.01 to 0.5 mol per 1 mol of compound (Ib).

[0518] In the reaction, the oxidizing agent is usually used in a ratio of 1 to 2 mol based on 1 mol of compound (Ib).

[0519] The reaction temperature is usually within the range of -20 to 120° C. The reaction time is usually within the range of 0.1 to 12 hours.

[0520] After the reaction is completed, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of an alkali (e.g., sodium bicarbonate) as needed. The organic layer is dried and concentrated to obtain compound (Ic).

[0521] Alternatively, compound (Ic) can also be produced in a one-step reaction (one pot) by reacting compound (Ia) with an oxidizing agent.

[0522] The reaction can be carried out by producing Compound (Ic) from Compound (Ib) using an oxidizing agent in a ratio of usually 2 to 5 mol relative to 1 mol of Compound (Ia).

[0523] Manufacturing method 2

[0524] The compound represented by formula (I-1-A) (hereinafter referred to as compound (I-1-A)) can be produced by reacting a compound represented by formula (M1-1-A) (hereinafter referred to as compound (M1-1-A)) with a compound represented by formula (M2-1) (hereinafter referred to as compound (M2-1)) in the presence of a condensing agent.

[0525] [Chemical Formula 7]

[0526]

[0527] [Where R A represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group E, a phenyl group which may be substituted by one or more substituents selected from Group F, or a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group F. Other symbols have the same meanings as above.]

[0528] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers (hereinafter referred to as ethers) such as tetrahydrofuran (hereinafter referred to as THF) and methyl tert-butyl ether (hereinafter referred to as MTBE); halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic hydrocarbons); esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters); nitriles; aprotic polar solvents (hereinafter referred to as aprotic polar solvents) such as N-methylpyrrolidone (hereinafter referred to as NMP), N,N-dimethylformamide (hereinafter referred to as DMF), and dimethyl sulfoxide (hereinafter referred to as DMSO); nitrogen-containing aromatic compounds (hereinafter referred to as nitrogen-containing aromatic compounds) such as pyridine, picoline, lutidine, and quinoline; and mixtures of two or more thereof.

[0529] Examples of the condensing agent used in the reaction include carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[0530] A catalyst may be used as needed in the reaction. Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole. When a catalyst is used in the reaction, the catalyst is usually used in a ratio of 0.01 to 0.5 mol relative to 1 mol of compound (M1-1-A).

[0531] In the reaction, a base may be used as needed. Examples of the base used in the reaction include organic bases such as triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases). When a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (M1-1-A).

[0532] In the reaction, the compound (M2-1) is usually used in a ratio of 1 to 2 mol, and the condensing agent is usually used in a ratio of 1 to 2 mol, based on 1 mol of the compound (M1-1-A).

[0533] The reaction temperature is usually in the range of 0 to 200° C. The reaction time is usually in the range of 0.1 to 12 hours.

[0534] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (I-1-A).

[0535] Compound (M2-1) is a commercially available compound or can be produced by a known method.

[0536] Manufacturing method 3

[0537] Compound (I-1-A) can also be produced by reacting compound (M1-1-A) with a compound represented by formula (M2-2) (hereinafter referred to as compound (M2-2)).

[0538] [Chemical Formula 8]

[0539]

[0540] [In the formula, the symbols have the same meanings as above.]

[0541] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers; aliphatic hydrocarbons such as hexane, heptane, and octane (hereinafter referred to as aliphatic hydrocarbons); aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles; aprotic polar solvents; and mixtures of two or more thereof.

[0542] A base may be used in the reaction as needed. Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); and organic bases. When a base is used in the reaction, the base is generally used in a ratio of 1 to 2 moles per 1 mole of compound (M1-1-A).

[0543] In the reaction, compound (M2-2) is usually used in a ratio of 0.8 to 1.2 mol based on 1 mol of compound (M1-1-A).

[0544] The reaction temperature is usually within the range of -20 to 200° C. The reaction time is usually within the range of 0.1 to 24 hours.

[0545] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (I-1-A).

[0546] Compound (M2-2) is a commercially available compound or can be produced by a known method.

[0547] Manufacturing Method 4

[0548] The compound represented by formula (I-2-B) (hereinafter referred to as compound (I-2-B)) can be produced by reacting a compound represented by formula (II) (hereinafter referred to as compound (II)) with a compound represented by formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of a base.

[0549] [Chemical Formula 9]

[0550]

[0551] [Where R B represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group E, C(O)R 4 、C(O)OR 4 or C(O)NR 4 R 5 , L represents a leaving group such as a chlorine atom or a bromine atom, and other symbols have the same meanings as above.]

[0552] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more thereof.

[0553] Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides), alkali metal carbonates, and organic bases.

[0554] In the reaction, the compound (R-1) is usually used in a ratio of 1 to 5 mol, and the base is usually used in a ratio of 1 to 2 mol, based on 1 mol of the compound (II).

[0555] The reaction temperature is usually within the range of 0 to 100° C. The reaction time is usually within the range of 0.1 to 24 hours.

[0556] After the reaction is completed, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (I-2-B).

[0557] Compound (R-1) is a commercially available compound or can be produced by a known method.

[0558] Manufacturing method 5

[0559] The compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting a compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2)) with a compound represented by formula (M2-3) (hereinafter referred to as compound (M2-3)).

[0560] [Chemical Formula 10]

[0561]

[0562] [Where V 1 represents a halogen atom, and other symbols have the same meanings as above.]

[0563] In V 1 When it is a fluorine atom, compound (I-1) can be produced by reacting compound (M1-2) with compound (M2-3) in the presence of a base.

[0564] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more thereof.

[0565] Examples of the base used in the reaction include alkali metal carbonates and alkali metal hydrides.

[0566] In the reaction, the compound (M2-3) is usually used in a ratio of 0.8 to 1.2 mol, and the base is usually used in a ratio of 1 to 2 mol, based on 1 mol of the compound (M1-2).

[0567] The reaction temperature is usually in the range of 0 to 200° C. The reaction time is usually in the range of 0.5 to 24 hours.

[0568] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (I-1).

[0569] In V 1In the case of a chlorine atom, a bromine atom or an iodine atom, compound (I-1) can be produced by reacting compound (M1-2) with compound (M2-3) in the presence of a base and a copper catalyst or a palladium catalyst.

[0570] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more thereof.

[0571] Examples of the base used in the reaction include alkali metal carbonates; phosphates such as trisodium phosphate and tripotassium phosphate; alkali metal hydrides; organic bases; and cyclic amines such as 1,4-diazabicyclo[2,2,2]octane and diazabicycloundecene.

[0572] Examples of the copper catalyst used in the reaction include copper (I) iodide, copper (I) bromide, copper (I) chloride, and copper (I) oxide. When a copper catalyst is used in the reaction, it is usually used in a ratio of 0.01 to 0.5 mol per 1 mol of compound (M1-2).

[0573] Examples of the palladium catalyst used in the reaction include palladium(II) acetate and tris(dibenzylideneacetone)dipalladium(0). When a palladium catalyst is used in the reaction, it is usually used in a ratio of 0.01 to 0.2 mol based on 1 mol of compound (M1-2).

[0574] A ligand may be used in the reaction as needed. Examples of ligands include acetylacetone, salen, phenanthroline, triphenylphosphine, and 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene. When a ligand is used in the reaction, it is generally used in a ratio of 0.01 to 0.5 mol per 1 mol of compound (M1-2).

[0575] In the reaction, the compound (M2-3) is usually used in a ratio of 0.8 to 1.2 mol, and the base is usually used in a ratio of 1 to 2 mol, based on 1 mol of the compound (M1-2).

[0576] The reaction temperature is usually in the range of 0 to 200° C. The reaction time is usually in the range of 0.5 to 24 hours.

[0577] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (I-1).

[0578] In compound (M2-3), R 1 R A or R BThe compound is a commercially available compound or can be produced by a known method.

[0579] Manufacturing Method 6

[0580] Compound (Ia) can be produced according to the following synthetic route.

[0581] [Chemical Formula 11]

[0582]

[0583] [Where, X a represents a chlorine atom, a bromine atom or an iodine atom, X b Indicates SR 2 or hydrogen atom, and other symbols have the same meanings as above.]

[0584] First, a step (hereinafter referred to as step 6-A) of producing a compound represented by formula (M3-1) (hereinafter referred to as compound (M3-1)) from a compound represented by formula (III-1) (hereinafter referred to as compound (III-1)) will be described.

[0585] Compound (M3-1) can be produced by reacting compound (III-1) with a halogenating agent.

[0586] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof.

[0587] Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide.

[0588] In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 mol based on 1 mol of compound (III-1).

[0589] The reaction temperature is usually within a range of -20°C to 200°C, and the reaction time is usually within a range of 0.1 to 72 hours.

[0590] After the reaction is completed, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (M3-1).

[0591] Next, the process for producing compound (Ia) from compound (M3-1) will be described.

[0592] Compound (Ia) can be produced by reacting compound (M3-1) with a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)) in the presence of a metal catalyst and a base.

[0593] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more thereof.

[0594] Examples of the metal catalyst used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride.

[0595] Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0596] A ligand may also be used in the reaction. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, it is generally used in a ratio of 0.01 to 1 mol per 1 mol of compound (M3-1).

[0597] In the reaction, compound (R-2) is usually used in a ratio of 1 to 20 mol, the metal catalyst is usually used in a ratio of 0.01 to 0.5 mol, and the base is usually used in a ratio of 0.1 to 5 mol, based on 1 mol of compound (M3-1).

[0598] The reaction temperature is usually within a range of -20°C to 200°C, and the reaction time is usually within a range of 0.1 to 72 hours.

[0599] After the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (Ia).

[0600] Compound (R-2) is known or can be produced according to a known method.

[0601] Next, the process for producing compound (Ia) from compound (III-1) will be described.

[0602] Compound (Ia) can also be produced by reacting Compound (III-1) with a compound represented by formula (R-3) (hereinafter referred to as Compound (R-3)) in the presence of a halogenating agent.

[0603] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more thereof.

[0604] Examples of the halogenating agent include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, and potassium iodide.

[0605] In the reaction, an oxidizing agent may be used as needed. Examples of the oxidizing agent used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, DMSO, and the like. When an oxidizing agent is used in the reaction, the oxidizing agent is usually used in a ratio of 1 to 20 moles relative to 1 mole of compound (III-1).

[0606] In the reaction, the compound (R-3) is usually used in a ratio of 0.5 to 10 mol, and the halogenating agent is usually used in a ratio of 0.05 to 10 mol, based on 1 mol of the compound (III-1).

[0607] The reaction temperature is usually in the range of 0° C. to 200° C. The reaction time is usually in the range of 0.1 to 72 hours.

[0608] After the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (Ia).

[0609] Compound (R-3) is known or can be produced according to a known method.

[0610] Manufacturing Method 7

[0611] The compound represented by formula (IS) (hereinafter referred to as compound (IS)) can be produced by reacting compound (I-1) with a sulfiding agent.

[0612] [Chemical Formula 12]

[0613]

[0614] [In the formula, the symbols have the same meanings as above.]

[0615] The reaction can be carried out in the presence of a solvent or in the absence of a solvent. Examples of the solvent include ethers, halogenated hydrocarbons, aromatic hydrocarbons, nitriles, nitrogen-containing aromatic compounds, and mixtures of two or more thereof.

[0616] Examples of the sulfurizing agent include phosphorus pentasulfide and Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphatane-2,4-disulfide).

[0617] In the reaction, the sulfiding agent is usually used in a ratio of 1 to 3 mol based on 1 mol of compound (I-1).

[0618] The reaction temperature is usually in the range of 0° C. to 200° C. The reaction time is usually in the range of 1 to 24 hours.

[0619] After the reaction is completed, water is added to the reaction mixture, extraction is carried out with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain Compound (IS).

[0620] Manufacturing method 8

[0621] The compound represented by formula (II-S) (hereinafter referred to as compound (II-S)) can be produced by reacting compound (II-O) with a sulfiding agent.

[0622] [Chemical Formula 13]

[0623]

[0624] [In the formula, the symbols have the same meanings as above.]

[0625] The reaction can be carried out according to Production Method 7 using Compound (II-0) in place of Compound (I-1).

[0626] The compound represented by formula (II-SB) can be produced from compound (II-S) according to Production Method 4.

[0627] [Chemical Formula 14]

[0628]

[0629] [In the formula, the symbols have the same meanings as above.]

[0630] Manufacturing method 9

[0631] The N-oxide of the compound represented by formula (I) can be produced by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be carried out according to, for example, the method described in Production Method 1, U.S. Patent Application Publication No. 2018 / 0009778, or International Publication No. 2016 / 121970.

[0632] The following describes a method for producing the intermediate.

[0633] Reference manufacturing method 1

[0634] The compound represented by formula (M1-1-D) (hereinafter referred to as compound (M1-1-D)) can be produced by reacting a compound represented by formula (M1-3) (hereinafter referred to as compound (M1-3)) with a compound represented by formula (R-5) (hereinafter referred to as compound (R-5)) in the presence of a base.

[0635] [Chemical Formula 15]

[0636]

[0637] [Where R D represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group D, or a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group E, and other symbols have the same meanings as above.]

[0638] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more thereof.

[0639] Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0640] In the reaction, the compound (R-5) is usually used in a ratio of 1 to 5 mol, and the base is usually used in a ratio of 1 to 2 mol, based on 1 mol of the compound (M1-3).

[0641] The reaction temperature is usually within the range of 0 to 100° C. The reaction time is usually within the range of 0.1 to 24 hours.

[0642] After the reaction is completed, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (M1-1-D).

[0643] Reference Manufacturing Method 2

[0644] Compound (M1-1-A) can be produced by reacting a compound represented by formula (M1-2-2) (hereinafter referred to as compound (M1-2-2)) with a compound represented by formula (R-6) (hereinafter referred to as compound (R-6)).

[0645] [Chemical Formula 16]

[0646]

[0647] [Where, X d represents a fluorine atom or a chlorine atom, and other symbols have the same meanings as above.]

[0648] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include aprotic polar solvents, alcohols, and mixtures of two or more thereof.

[0649] In the reaction, a base may be used as needed. Examples of the base used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 mol relative to 1 mol of compound (M1-2-2).

[0650] In the reaction, the compound (R-6) is usually used in a ratio of 1 to 100 mol based on 1 mol of the compound (M1-2-2).

[0651] The reaction temperature is usually in the range of 25° C. to 200° C. The reaction time is usually in the range of 0.1 to 48 hours.

[0652] After the reaction is completed, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (M1-1-A).

[0653] Compound (R-6) is a commercially available compound or can be produced by a known method.

[0654] Reference Manufacturing Method 3

[0655] Compound (M1-3) can be produced by reacting compound (M1-2-2) with ammonia.

[0656] [Chemical Formula 17]

[0657]

[0658] [In the formula, the symbols have the same meanings as above.]

[0659] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, nitriles, aprotic polar solvents, alcohols, water, and mixtures of two or more thereof.

[0660] In the reaction, a base may be used as needed. Examples of the base used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 mol relative to 1 mol of compound (M1-2-2).

[0661] Ammonia can also be used in the form of a solution such as aqueous ammonia or methanolic ammonia solution.

[0662] In the reaction, ammonia is usually used in a ratio of 1 to 100 mol based on 1 mol of compound (M1-2-2).

[0663] The reaction temperature is usually in the range of -20°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours.

[0664] After the reaction is completed, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer can be performed to obtain compound (M1-3).

[0665] Reference Manufacturing Method 4

[0666] The compound represented by formula (M1-2b) and the compound represented by formula (M1-2c) can be produced by reacting the compound represented by formula (M1-2a) (hereinafter referred to as compound (M1-2a)) with an oxidizing agent. In addition, the compound represented by formula (M1-2c) can also be produced by reacting the compound represented by formula (M1-2b) with an oxidizing agent.

[0667] [Chemical Formula 18]

[0668]

[0669] [In the formula, the symbols have the same meanings as above.]

[0670] These reactions can be carried out according to Production Method 1.

[0671] Reference Manufacturing Method 5

[0672] Compound (M1-2a) can be produced according to the following synthesis route.

[0673] [Chemical Formula 19]

[0674]

[0675] [In the formula, the symbols have the same meanings as above.]

[0676] These reactions can be carried out according to Production Method 6.

[0677] The compound represented by formula (M1-4) (hereinafter referred to as compound (M1-4)) is known or can be produced according to the methods described in International Publication No. 2015 / 157093, International Publication No. 2016 / 109706, Organic & Biomolecular Chemistry, 2017, 15, 4199., and Europian Journal of Medicinal Chemistry, 2016, 123, 916.

[0678] Reference Manufacturing Method 6

[0679] Compound (II-0) can be produced by reacting compound (M1-3) with compound (M2-1) or compound (M2-2).

[0680] [Chemical Formula 20]

[0681]

[0682] [In the formula, the symbols have the same meanings as above.]

[0683] These reactions can be carried out according to Production Method 2 or Production Method 3 using Compound (M1-3) instead of Compound (M1-1-A).

[0684] Reference Manufacturing Method 7

[0685] The compound represented by formula (M3-1-A) can be produced by reacting a compound represented by formula (M1-6-A) (hereinafter referred to as compound (M1-6-A)) with compound (M2-1) or compound (M2-2).

[0686] [Chemical Formula 21]

[0687]

[0688] [In the formula, the symbols have the same meanings as above.]

[0689] These reactions can be carried out according to Production Method 2 or Production Method 3 using Compound (M1-6-A) instead of Compound (M1-1-A).

[0690] Reference Manufacturing Method 8

[0691] The compound represented by formula (M1-6-D) (hereinafter referred to as compound (M1-6-D)) can be produced according to the following synthesis route.

[0692] [Chemical Formula 22]

[0693]

[0694] [In the formula, the symbols have the same meanings as above.]

[0695] First, a method for producing a compound represented by formula (M1-7) (hereinafter referred to as compound (M1-7)) will be described.

[0696] Compound (M1-7) can be produced by reacting a compound represented by formula (M1-5) (hereinafter referred to as compound (M1-5)) with ammonia. The reaction can be carried out according to Reference Production Method 3 using compound (M1-5) instead of compound (M1-2-2).

[0697] Next, the method for producing compound (M1-6-D) will be described.

[0698] Compound (M1-6-D) can be produced by reacting Compound (M1-7) with Compound (R-5) in the presence of a base. The reaction can be carried out according to Reference Production Method 1 using Compound (M1-7) instead of Compound (M1-3).

[0699] Reference Manufacturing Method 9

[0700] Compound (M1-6-A) can be produced according to the following synthesis route.

[0701] [Chemical Formula 23]

[0702]

[0703] [In the formula, the symbols have the same meanings as above.]

[0704] First, a method for producing the compound represented by formula (M1-8-A) (hereinafter referred to as compound (M1-8-A)) will be described.

[0705] Compound (M1-8-A) can be produced by reacting compound (M1-4) with compound (R-6). The reaction can be carried out according to Reference Production Method 2 using compound (M1-4) instead of compound (M1-2-2).

[0706] Next, the method for producing compound (M1-6-A) will be described.

[0707] Compound (M1-6-A) can be produced by reacting compound (M1-8-A) with a halogenating agent. The reaction can be carried out according to step 6-A of production method 6, using compound (M1-8-A) instead of compound (III-1).

[0708] Reference Manufacturing Method 10

[0709] The compound represented by formula (M3-1-B) (hereinafter referred to as compound (M3-1-B)) can be produced according to the following synthesis route.

[0710] [Chemical Formula 24]

[0711]

[0712] [In the formula, the symbols have the same meanings as above.]

[0713] First, a method for producing a compound represented by formula (M3-2) (hereinafter referred to as compound (M3-2)) will be described.

[0714] Compound (M3-2) can be produced by reacting compound (M1-7) with compound (M2-1) or compound (M2-2). These reactions can be carried out according to Production Method 2 or Production Method 3 using compound (M1-7) instead of compound (M1-1-A).

[0715] Next, a method for producing compound (M3-1-B) will be described.

[0716] Compound (M3-1-B) can be produced by reacting Compound (M3-2) with Compound (R-1) in the presence of a base. The reaction can be carried out according to Production Method 4 using Compound (M3-2) instead of Compound (II).

[0717] Reference Manufacturing Method 11

[0718] The compound represented by formula (III-1-A) (hereinafter referred to as compound (III-1-A)) can be produced according to the following synthesis route.

[0719] [Chemical Formula 25]

[0720]

[0721] [In the formula, the symbols have the same meanings as above.]

[0722] Compound (III-1-A) can be produced by reacting compound (M1-8-A) with compound (M2-1) or compound (M2-2). These reactions can be carried out according to Production Method 2 or Production Method 3 using compound (M1-8-A) instead of compound (M1-1-A).

[0723] Reference Manufacturing Method 12

[0724] The compound represented by formula (III-1-B) (hereinafter referred to as compound (III-1-B)) can be produced according to the following synthesis route.

[0725] [Chemical Formula 26]

[0726]

[0727] [In the formula, the symbols have the same meanings as above.]

[0728] First, a method for producing the compound represented by formula (III-2-B) (hereinafter referred to as compound (III-2-B)) will be described.

[0729] Compound (III-2-B) can be produced by reacting a compound represented by formula (M1-9) (hereinafter referred to as compound (M1-9)) with compound (M2-1) or compound (M2-2). These reactions can be carried out according to Production Method 2 or Production Method 3 using compound (M1-9) instead of compound (M1-1-A).

[0730] Next, a method for producing compound (III-1-B) will be described.

[0731] Compound (III-1-B) can be produced by reacting Compound (III-2-B) with Compound (R-1) in the presence of a base. The reaction can be carried out according to Production Method 4 using Compound (III-2-B) instead of Compound (II).

[0732] Reference manufacturing method 13

[0733] Compound (M1-9) can be produced by reacting compound (M1-4) with ammonia.

[0734] [Chemical Formula 27]

[0735]

[0736] [In the formula, the symbols have the same meanings as above.]

[0737] The reaction can be carried out according to Reference Production Method 3 using Compound (M1-4) instead of Compound (M1-2-2).

[0738] The compound of the present invention may be mixed or used in combination with one or more components (hereinafter referred to as present components) selected from the following group consisting of Group (a), Group (b), Group (c) and Group (d).

[0739] The aforementioned mixed use or combined use means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval therebetween.

[0740] When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in the same preparation.

[0741] One aspect of the present invention is a composition (hereinafter referred to as composition A) comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d) (i.e., the present component) and the compound of the present invention.

[0742] Group (a) is composed of acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABA-gated chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chord organ TRPV channel modulators, mite growth inhibitors, and insect midgut lining disruption agents derived from microorganisms. The present invention relates to a group consisting of: a group consisting of: inhibitors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin-based insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III, and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ranolidine receptor modulators (e.g., diamide-based insecticides), chord organ modulators, microbial insecticides, and other insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients. These ingredients are described according to the classification based on the IRAC mechanism of action.

[0743] Group (b) includes nucleic acid synthesis inhibitors (e.g., phenylamide-based fungicides, acylamino acid-based fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine-based fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., triazole-based DMI fungicides), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These ingredients are described according to the FRAC-based mechanism of action.

[0744] Group (c) is a group of plant growth regulating ingredients (including mycorrhizal fungi and rhizobia).

[0745] Group (d) is a group of repellent ingredients.

[0746] Examples of combinations of this component and the compound of the present invention are described below. For example, alanycarb+SX refers to a combination of alanycarb and SX.

[0747] It should be noted that the abbreviation SX refers to any one compound of the present invention selected from the compound group SX1 to SX1908. In addition, the ingredients described below are all known ingredients and can be obtained from commercially available preparations or manufactured by known methods. If the ingredient is a microorganism, it can also be obtained from a bacterial collection institution. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[0748] Combination of the present component of the above group (a) with the compound of the present invention:

[0749] Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide phosphide)+SX, amitraz+SX, azadirachtin+SX, azamethiphos+SX, azinphos-ethyl+SX, azinphos-methyl+SX, azocyclotin+SX, bark of Celastrus angulatus)+SX, bendiocarb+SX, benfluthrin+SX, benfuracarb+SX, bensultap+SX, benzoximate+SX, benzpyrimoxan+SX, beta-cyfluthrin+SX, beta-cypermethrin+SX, bifenazate+SX, bifenthrin+SX, bioallethrin+SX, bioresmethrin+SX, bistrifluron+SX, borax+SX, boric acid acid)+SX, broflanilide+SX, bromopropylate+SX, buprofezin+SX, butocarboxim+SX, butoxycarboxim+SX, cadusafos+SX, calcium phosphidephosphide)+SX, carbaryl+SX, carbofuran+SX, carbosulfan+SX, cartap hydrochloride hydrochloride) + SX, cartap + SX, chinomethionat + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin AA) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflumizone + SX, flanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate octaborate)+SX, disulfoton+SX, DNOC(2-methyl-4,6-dinitrophenol+SX, doramectin+SX, dried leaves of Dryopterisfilix-mas)+SX, emamectin-benzoate+SX, empenthrin+SX, endosulfan+SX, EPN(O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX, epsilon-metofluthrin+SX, epsilon-momfluorothrin+SX, esfenvalerate+SX, ethiofencarb+SX, ethion+SX, ethiprole+SX, ethoprophos+SX, etofenprox+SX, etoxazole+SX, extract of Artemisia absinthium+SX, extract of neem Azadirachta indica extract + SX, Cassia nigricans extract + SX, butterfly pea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tanacetum vulgare extract + SX, Urtica dioica extract + SX, Viscum album extract + SX, famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatinoxide)+SX, fenitrothion+SX, fenmezoditiaz+SX, fenobucarb+SX, fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX, fenvalerate+SX, fipronil+SX, flometoquin+SX, flonicamid+SX, fluacrypyrim+SX, fluazaindolizine+SX, fluazuron+SX, flubendiamide+SX, fluchlordiniliprole+SX, flucycloxuron+SX, flucythrinate+SX, Fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide (GS-omega / kappa HXTX-Hv1a peptide) + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acidacid)+SX, hydramethylnon+SX, hydroprene+SX, imicyafos+SX, imidacloprid+SX, imidaclothiz+SX, imiprothrin+SX, indazapyroxamet+SX, indoxacarb+SX, isocycloseram+SX, isofenphos+SX, isoprocarb+SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate thoxyaminothiophosphoryl)salicylate)+SX, isoxathion+SX, ivermectin+SX, kadethrin+SX, kappa-tefluthrin+SX, kappa-bifenthrin+SX, kinoprene+SX, lambda-cyhalothrin+SX, ledprona+SX, lenoremycin+SX, lepimectin+SX, lime sulfur sulfur)+SX, lotilaner+SX, lufenuron+SX, machine oil+SX, malathion+SX, mecarbam+SX, meperfluthrin+SX, metaflumizone+SX, metam+SX, methamidophos+SX, methidathion+SX, methiocarb+SX, methomyl+SX, methoprene+SX, methoxychlor+SX, methoxyfenozide+SX, methyl bromide bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycinoxime+SX, mivorilaner+SX, modoflaner+SX, momfluorothrin+SX, monocrotophos+SX, moxidectin+SX, naled+SX, nicofluprole+SX, nicotine+SX, nicotine-sulfate+SX, nitenpyram+SX, novaluron+SX, noviflumuron+SX, Chenopodium anthelminticum seed oil (oil of the seeds of Chenopodium anthelminticum)+SX, omethoate+SX, oxamyl+SX, oxazosulfyl+SX, oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, permethrin+SX, phenothrin+SX, phenthoate+SX, phorate+SX, phosalone+SX, phosmet et)+SX, phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propylene glycol alginateglycolalginate)+SX, prothiofos+SX, pyflubumide+SX, pymetrozine+SX, pyraclofos+SX, pyrethrins+SX, pyridaben+SX, pyridalyl+SX, pyridaphenthion+SX, pyrifluquinazone+SX, pyrimidifen+SX, pyri minostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfurylfluoride + SX, tartar emetic emetic)+SX, tau-fluvalinate+SX, tebufenozide+SX, tebufenpyrad+SX, tebupirimfos+SX, teflubenzuron+SX, tefluthrin+SX, temephos+SX, terbufos+SX, terpene components extracted from wormwoodThe constituents of the extract ofchenopodium ambrosioides near ambrosioides+SX、tetrachlorantraniliprole+SX、tetrachlorvinphos+SX、tetradifon+SX、tetramethrin+SX、tetramethylfluthrin+SX、tetraniliprole+SX、theta-cypermethrin+SX、thiacloprid+SX、thiamethoxam+SX、thiocyclam+SX、thiodicarb+SX、thiofanox+SX、thiometon+SX、thiosultap-disodium+SX、thiosultap-sodium ultap-monosodium+SX, tigolaner+SX, tiorantraniliprole+SX, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, trifluenfuronate+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, umifoxolaner+SX, vamidothion+SX, wood extract of Quassia sylvatica extract of Quassia amara)+SX, XMC (3,5-dimethylphenyl N-methylcarbamate)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zinc phosphidephosphide) + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietane-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methyl sulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)propionamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propionamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09- 3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropane-2-yl]-2 -(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, 7-fluoro-N-[1-(methylsulfonyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one(2607927-97-7)+SX, BT crop protein Cry1Ab(BT crop protein Cry1Ab)+SX, BT crop protein Cry1Ac(BT crop protein Cry1Ac)+SX, BT crop protein Cry1Fa(BT crop105)+SX, BT crop protein Cry1A.105+SX, BT crop protein Cry2Ab+SX, BT crop protein Vip3A+SX, BT crop protein mCry3A+SX, BT crop protein Cry3Ab+SX, BT crop protein Cry3Ab+SX, BT crop protein Cry3Bb+SX, BT crop protein Cry3Bb+SX, BT crop protein Cry34Ab1 / Cry35Ab1+SX, Adoxophyes orana GV(granulovirus)strain BV-0001+SX, Anticarsia gemmatalis nuclear polyhedrosis virus MNPV (multiple nucleocapsid nucleopolyhedrovirus))+SX, Autographa californica MNPV+SX, Cydia pomonella GV strain V15+SX, Cydia pomonella GV strain V22+SX, Cryptophlebia leucotreta GV+SX, Dendrolimus punctatus cypovirus+SX, Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003+SX, Helicoverpa zea mays NPV+SX NPV)+SX, Lymantria dispar NPV+SX, Mamestra brassicae NPV+SX, Mamestra configurata NPV+SX, Neodiprion abietis NPV+SX,SX, Neodiprion lecontei NPV+SX, Neodiprion lecontei NPV+SX, Neodiprion sertifer NPV+SX, Nosema locustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodoptera exigua MNPV+SX, Spodoptera littoralis MNPV+SX, Spodoptera litura NPV+SX, NPV)+SX, Arthrobotrysdactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637+SX, Bacillus megaterium+SX, Bacillus sp. strain AQ175+SX, Bacillus sp. strain AQ177+SX, Bacillus sp. strain AQ178+SX, Bacillus sphaericus strain 2362 serotype H5a5b 2362serotypeH5a5b)+SX, Bacillus sphaericus strain ABTS1743+SX, Bacillus thuringiensis strain AQ52+SX, Bacillus thuringiensis strain BD#32+SX, Bacillus thuringiensis strain CR-371+SX,CR-371)+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200+SX, Bacillus thuringiensis subsp. Aizawai Serotype H-7+SX H-7)+SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351+SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123+SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306+SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348+SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841+SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841)+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19+SX, Bacillus thuringiensis subsp. Kurstaki strain F810+SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1+SX,strain HD-1)+SX, Bacillus thuringiensis subsp. Kurstaki strain PB54+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002+SX, Bacillus thuringiensis subsp. Morrison strain subsp.morrisoni)+SX, Bacillus thuringiensis var.colmeri+SX, Bacillus thuringiensis var.darmstadiensis strain 24-91+SX, Bacillus thuringiensis var.dendrolimus+SX, Bacillus thuringiensis var.galleriae+SX, Bacillus thuringiensis var.israelensis strain BMP144+SX, Bacillus thuringiensis var.israelensis serotype H-14+SX H-14)+SX, Bacillus thuringiensis var.japonensis strainbuibui)+SX, Bacillus thuringiensis var.sandiego strain M-7M-7)+SX, Bacillus thuringiensis var.7216+SX, Bacillus thuringiensis var.aegypti+SX, Bacillus thuringiensis var.T36+SX, Beauveria bassiana strain ANT-03+SX, Beauveria bassiana strain ATCC74040+SX, Beauveria bassiana strain GHA+SX, Beauveria brongniartii+SX, new heat-killed bacteria A396 strain (Burkholderia rinojensis strain A396)+SX, Chromobacterium subtsugae strain PRAA4-1T+SX, Dactyllela ellipsospora+SX, Dectylaria thaumasia+SX, Hirsutella minnesotensis+SX, Hirsutella rhossiliensis+SX, Hirsutella thompsonii+SX, Lagenidium giganteum+SX, Lecanicillium lecanii strain KV01+SX, Lecanicillium lecanii conidia of strain DAOM198499+SX, Lecanicillium lecanii conidia of strain DAOM198499+SX, Lecanicillium lecanii conidia of strain DAOM216596+SX, conidia of strain DAOM216596)+SX, Lecanicillium muscarium strain Ve6+SX, Metarhizium anisopliae strain F52+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. microsporum BIPESCO5 / F52 strain (Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52) + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticillium lecani strain NCIM1312+SX, Wolbachia pipientis+SX.

[0750] Combination of the present component of the above group (b) with the compound of the present invention:

[0751] Acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate sulfate)+SX, benalaxyl+SX, benalaxyl-M+SX, benodanil+SX, benomyl+SX, benthiavalicarb+SX, bethiavalicarb-isopropyl+SX, benzovindiflupyr+SX, binapacryl+SX, biphenyl+SX, bitertanol+SX, bixafen+SX, blasticidin-S+SX, Bordeaux mixture mixture)+SX, boscalid+SX, bromothalonil+SX, bromuconazole+SX, bupirimate+SX, captafol+SX, captan+SX, carbendazim+SX, carboxin+SX, carpropamid+SX, chinomethionat+SX, chitin+SX, chloroinconazide+SX, chloroneb+SX, chlorothalonil+SX, chlozolinate+SX, colletochlorin B+SX, copper(II) acetate+SX, copper(II) hydroxide+SX, copperoxychloride+SX, copper(II) sulfate+SX, coumoxystrobin+SX, cyazofamid+SX, cyflufenamid+SX,Cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX X, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX, dodecylbenzenesulphonic acid bis(ethylenediamine)copper(II) complex salt acid bisethylenediamine copper(II) salt)+SX, dodemorph+SX, dodine+SX, edifenphos+SX, enoxastrobin+SX, epoxiconazole+SX, etaconazole+SX, ethaboxam+SX, ethirimol+SX, etridiazole+SX, garlic extract+SX, extract of the cotyledons of lupine plantlets ("BLAD")+SX, extract of Equisetum arvense+SX, extract of Melaleuca alternifolia+SX, extract of Reynoutria sachalinensis+SX, extract of Nasturtium officinale+SX Tropaeolum majus)+SX,Famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, fentin acetate + SX, fentin chloride + SX, and fentin hydroxide. hydroxide)+SX, ferbam+SX, ferimzone+SX, florylpicoxamid+SX, fluazinam+SX, flubeneteram+SX, fludioxonil+SX, flufenoxadiazam+SX, flufenoxystrobin+SX, fluindapyr+SX, flumetylsulforim+SX, flumorph+SX, fluopicolide+SX, fluopyram+SX, fluopimomide+SX, fluoroimide+SX, fluoxapiprolin+SX , fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetyl-aluminium + SX, fuberidazole + SX, furaxyl + SX, furametpyr + SX, guazatine + SX,Hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate triacetate+SX, inpyrfluxam+SX, iodocarb+SX, ipconazole+SX, ipfentrifluconazole+SX, ipflufenoquin+SX, iprobenfos+SX, iprodione+SX, iprovalicarb+SX, isofetamid+SX, isofluxypram+SX, isoprethiolane+SX, isopyrazam+SX, isotianil+SX, kasugamycin+SX, kresoxim-methyl+SX, laminarin+SX, leaves and bark of oak ofQuercus)+SX, mancozeb+SX, mandestrobin+SX, mandipropamid+SX, maneb+SX, mefentrifluconazole+SX, mepanipyrim+SX, mepronil+SX, meptyldinocap+SX, metalaxyl+SX, metalaxyl-M+SX, metarylpicoxamid+SX, metconazole azole)+SX, methasulfocarb+SX, metiram+SX, metominostrobin+SX, metrafenone+SX, metyltetraprole+SX, myclobutanil+SX, naftifine+SX, nuarimol+SX, octhilinone+SX, ofurac+SX, orysastrobin+SX, oxadixyl+SX,Oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX,Pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, Saponins of Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium bicarbonate hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX , tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, validamycin + SX, valifenalate + SX,Vinclozolin + SX, yellow mustard powder + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidine (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N N-ethyl-N-methylformamidine (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidine (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidine (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl] 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, (2Z)-3-amino-2-cyano-3- Ethyl phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX,(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol(1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol(1394057-13-6)+SX, (1R,2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol(1801930-08-4)+SX, (1S, 2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentane-1-ol(1801930-09-5)+SX, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentane-1-carboxylate(1791398-02-1)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol(2019215-86-0)+SX, 1-(2,4- 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)- 1-(triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX,2-(Difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(Difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide -yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-yl]phenyl}methyl)isoxazolin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-acetyl-2-(ethylsulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9)+SX,N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindol-1-yl)butan-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]- L-alanine 3-(3,5-dichloropyridin-2-yl)butyl-2-yl ester + SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)butyl-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX、N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate(1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl Ester((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl Ester N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX,3,3,3-Trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide+SX, N-methoxy-N-methyl-N'-({4-[5-(trifluoromethyl) )-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N-diethyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea methyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1, 2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX,N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide+SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide+SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine+SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+SX, 2-[2-chloro-4-(4-chlorophenoxy)benzamide 2-[(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid methyl ester + SX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid ethyl ester + SX, 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid methyl ester + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX , 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester + SX, 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester + SX, 6-chloro- 3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX,2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl) amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-{[(oxetane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, fluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine pyrimidine-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidine-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidine-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidine-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX,3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, Pyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[ (E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, oxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide+SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide+SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide+SX,Methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate+SX, Methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate+SX, Methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate+SX, -2-methylphenyl}methyl)carbamic acid methyl ester + SX, (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-2-propenoic acid methyl ester + SX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-2-propenoic acid methyl ester + SX, (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxy-2-propenoic acid methyl ester Ester + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dihydroisoquinoline Methyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]-2-propenoic acid methyl ester + SX, radioactive Agrobacterium K1026 strain (Agrobacterium radiobactor strain K1026) + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo (trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX,Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate B246 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate B246 + SX, Bacillus amyloliquefaciens strain Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus QST2808 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus pumilus strain strain QST2808)+SX, Bacillus simplex strain CGF2856+SX,Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain HAI0404)+SX, Bacillus subtilis strain IAB / BS03+SX, Bacillus subtilis strain MBI600+SX, Bacillus subtilis QST30002 / AQ30002+SX, Bacillus subtilis QST30004 / AQ30004+SX, Bacillus subtilis QST713+SX, Bacillus subtilis QST714+SX QST714)+SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24+SX, Bacillus subtilis strain Y1336+SX, Burkholderia cepacia+SX, Burkholderia cepacia type Wisconsin strain J82+SX,Burkholderia cepacia type Wisconsin M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, Cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, CGE234M403)+SX, Fusarium oxysporum strain Fo47+SX, Gliocladium catenulatum strain J1446+SX, Paenibacillus polymyxa strain AC-1+SX, Paenibacillus polymyxa strain BS-0105+SX, Pantoea agglomerans strain E325+SX, Phlebiopsis gigantea strain VRA1992+SX, Pseudomonas aureofaciens strain TX-1+SX TX-1)+SX, Pseudomonas chlororaphis strain 63-28+SX, Pseudomonas chlororaphis strain AFS009+SX, Pseudomonas chlororaphis strain MA342+SX,Pseudomonas fluorescens strain 1629RS+SX, Pseudomonas fluorescens strain A506+SX, Pseudomonas fluorescens strain CL145A+SX, Pseudomonas fluorescens strain G7090+SX, Pseudomonas sp. strain CAB-02+SX, Pseudomonas syringae strain 742RS+SX, Pseudomonas syringae strain MA-4+SX, Pseudomonas flocculatus+SX PF-A22UL strain + SX, Pseudomonas rhodesia strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX SAY-Y-94-01)+SX, Talaromyces flavus strain V117b+SX, Trichoderma asperellum strain ICC012+SX, Trichoderma asperellum SKT-1+SX, Trichoderma asperellum strain T25+SX,Trichoderma asperellum strain T34+SX, Trichoderma asperellum strain TV1+SX, Trichoderma atroviride strain CNCM 1-1237+SX, Trichoderma atroviridestrain LC52+SX, Trichoderma atroviridestrain IMI 206040+SX, Trichoderma atroviride strain SC1+SX, Trichoderma atroviride strain SKT-1+SX, Trichoderma atroviride strain T11+SX, Trichoderma gamsii endophytic fungus ICC080+SX strain ICC080)+SX, Trichoderma harzianum strain 21+SX, Trichoderma harzianum strain DB104+SX, Trichoderma harzianum strain DSM 14944+SX, Trichoderma harzianum strain ESALQ-1303+SX, Trichoderma harzianum strain ESALQ-1306+SX, Trichoderma harzianum strain IIHR-Th-2+SX, Trichoderma harzianum strain ITEM908+SX, Trichoderma harzianum kd+SX, Trichoderma harzianum strain ESALQ-1303+SX, Trichoderma harzianum strain ESALQ-1306+SX, Trichoderma harzianum strain IIHR-Th-2+SX, Trichoderma harzianum strain ITEM908+SX, Trichoderma harzianum kd+SX, Trichoderma harzianum strain ESALQ-1306+SX, Trichoderma harzianum strain IIHR-Th-2+SX, Trichoderma harzianum strain ITEM908+SX, Trichoderma harzianum kd+SX, Trichoderma harzianum strain ESALQ-1303+SX, Trichoderma harzianum strain ESALQ-1306+SX, Trichoderma harzianum strain IIHR-Th-2+SX, Trichoderma harzianum strain harzianum strain kd)+SX, Trichoderma harzianum strain MO1 (Trichoderma harzianumstrain MO1)+SX, Trichoderma harzianum strain SF (Trichoderma harzianum strain SF)+SX,Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, Trichoderma astromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 CGF4526)+SX, Harpin protein+SX.

[0752] Combination of the present component of the above group (c) with the compound of the present invention:

[0753] 1-Methylcyclopropene+SX, 1,3-diphenylurea+SX, 2,3,5-triiodobenzoic acid+SX, IAA((1H-indol-3-yl)acetic acid)+SX, IBA(4-(1H-indol-3-yl)butyric acid)+SX, MCPA(2-(4-chloro-2-methylphenoxy)acetic acid)+SX, MCPB(4-(4-chloro-2-methylphenoxy)butyric acid)+SX, 4-CPA(4-chlorophenoxyacetic acid) acid + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloridechloride + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, Gibberellin A A) + SX, Gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat-chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione-calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintofen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate cyanate) + SX, thidiazuron + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX, uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid methyl ester + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomusetunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 strain + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH strain + SX, Azospirillum brasilense Ab-V5 strain + SX, Azospirillum brasilense Ab-V6 strain + SX, Azospirillum caulinodans + SX, Azospirillumhalopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 strain + SX, Bradyrhizobium elkanii SEMIA 5019 strain + SX, Bradyrhizobium japonicum TA-11 strain + SX, Bradyrhizobium USDA 110 strain + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 strain + SX, Mesorhizobium ciceri + SX, Mesorhizobium huaguihuakii)+SX, Mesorhizobium loti+SX, Rhizobium etli+SX, Rhizobium galegae+SX, Rhizobium leguminosarum bv.Phaseoli+SX, Rhizobium leguminosarum bv.Trifolii+SX, Rhizobium leguminosarum bv.Viciae+SX, Rhizobium trifolii+SX, Rhizobium tropici+SX, Sinorhizobium fredii+SX, Sinorhizobium truncatula meliloti)+SX, Zucchini Yellow Mosaik Virus weak strain+SX.

[0754] Combination of the present component of the above group (d) with the compound of the present invention:

[0755] Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0756] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, and 1:50 in terms of weight ratio (compound of the present invention:present component).

[0757] The compound of the present invention can control harmful arthropods such as harmful insects and harmful mites, harmful mollusks, and harmful nematodes. Examples of harmful arthropods, harmful mollusks, and harmful nematodes include the following.

[0758] Hemiptera: Laodelphax striatellus, Nilaparvatalugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodesorizicolus, Stenocranus pacificus, etc. Delphacidae; Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus spp. maidis), white-winged brown-veined leafhopper (Cofanaspectra), two-spotted green leafhopper (Amrasca biguttula biguttula), etc.; Aphrophoridae (Aphrophoridae) (Philaenus spumarius), etc.; Cercopidae (Mahanarvaposticata), sugarcane leafhopper (Mahanarva fimbriolata), etc.;Beet aphid (Aphisfabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), apple aphid (Aphis pomi), spiraea aphid (Aphis spiraecola), peach aphid (Myzus persicae), plum short-tailed aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), rose apple aphid (Dysaphis plantaginea), cabbage stalked aphid (Lipaphis erysimi), potato long-tailed aphid (Macrosiphum euphorbiae), eggplant ditch aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), cereal stalked aphid (Rhopalosiphumpadi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach pink aphid (Hyalopterus pruni), sorghum aphid (Melanaphis sacchari), Tetraneuranigriabdominalis, Ceratovacuna lanigera, Eriosomalanigerum, Sitobion avenae, and other Aphididae; Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, and other Phylloxeridae; Adelgidae, Adelges tsugae, Adelges piceae, and Aphrastasia pectinatae;Pentatomidae, including the black rice stink bug (Scotinophara lurida), the Malayan black rice stink bug (Scotinophara coarctata), the black-bearded rice stink bug (Nezara antennata), the northern two-star stink bug (Eysarcoris aeneus), the large-spined white-star stink bug (Eysarcoris lewisi), the broad two-star stink bug (Eysarcoris ventralis), the pseudo two-star stink bug (Eysarcoris annamita), the brown-winged stink bug (Halyomorpha halys), the green rice stink bug (Nezara viridula), the brown stink bug (Euschistus heros), the red-banded stink bug (Piezodorus guildinii), the rice stink bug (Oebalus pugnax), the stink bug (Dichelops melacanthus), the wall stink bug (Piezodorus hybneri); the digging brown stink bug (Scaptocoris castanea) and other Cydnidae; Alydidae such as Riptortus clavatus, Leptocorisa chinensis, and Leptocorisa acuta; Coreidae such as Cletus punctiger and Leptoglossus australis; Lygaeidae such as Cavelerius saccharivorus, Togohemipterus, and Blissus leucopterus; Trigonotylus caelestialium, Stenotus rubrovittatus, and Stenodema calcarata), American meadow bug (Lygus lineolaris), and other Miridae; Trialeurodes vaporariorum (Househouse whitefly), Bemisia tabaci (Bemisia tabaci), Dialeurodes citri (Citrus whitefly), Aleurocanthus spiniferus (Blackthorn whitefly), Aleurocanthus camelliae (Camellia whitefly), and Pealius euryae (Whitefly);Tea long round scale (Abgrallaspis cyanophylli), red round scale (Aonidiella aurantii), pear round scale (Diaspidiotusperniciosus), mulberry white scale (Pseudaulacaspis pentagona), arrow-pointed shield scale (Unaspis yanonensis), citrus sharp shield scale (Unaspis citri) and other shield scale families (Diaspididae); red wax scale (Ceroplastes rubens) and other scale families (Coccidae); blowing cotton scale (Icerya purchasi), silver-haired blowing cotton scale (Icerya seychellarum) and other cotton scale families (Margarodidae); Lycoris mealybug (Phenacoccus solani), hibiscus mealybug (Phenacoccussolenopsis), Japanese hip-striped mealybug (Planococcus Pseudococcidae, including Pseudococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, and Brevennia rehi; Psyllidae, including Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, and Cacopsylla pyricola; and Corythucha ciliata, Corythucha chrysanthemum. marmorata), Stephanitis nashi, and Stephanitis pyrioides, among others; Cimicidae, including Cimex lectularius and Cimex hemipterus; and Cicadidae, including Quesada gigas.Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, Rhodonius prolixus, and other members of the Reduviidae family.

[0759] Lepidoptera: Chilo suppressalis, Chilopolychrysus, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis, Hellulaundalis, Herpetogramma luctuosale, Parapedia siateterrellus, Nymphula depunctalis), sugarcane borer (Diatraea saccharalis), eggplant yellow moth (Leucinodes orbonalis) and other grass borers (Crambidae); small corn borer (Elasmopalpuslignosellus), Indian grain moth (Plodia interpunctella), leather dark moth (Euzophera batangensis), powdery moth (Cadra cautella) and other moths (Pyralidae);Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestrabrassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Agrotis segetum, Autographanigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis spp. virescens, Heliothis spp., Helicoverpa armigera, Helicoverpa zea, Anticarsia gemmatalis, Alabamaargillacea, Hydraecia immanis, and other Noctuidae species; and Pieridae such as Pieris rapae.Pear borer (Grapholita molesta), sand apple borer (Grapholita dimorpha), soybean borer (Leguminivora glycinivorella), Japanese bean moth (Matsumuraeses azukivora), apple leaf roller (Adoxophyesorana fasciata), tea leaf roller (Adoxophyes honmai), tea long leaf roller (Homona magnanima), apple yellow leaf roller (Archipsfuscocupreanus), apple leaf roller (Cydia pomonella), yellow stem borer (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit fly (Citripestissagittiferella), grape flower wing roller (Lobesia botrana), etc. (Tortricidae); tea leaf roller (Caloptilia theivora), golden leaf roller (Phyllonorycter ringoniella, etc.; Carposinidae, etc.; Lyonetiidae, etc.; Lymantriidae, etc.; Lymantria spp., etc.; Euproctis spp., etc.; Plutellidae, etc.; Anarsialineatella, etc.; Helcystogramma triannulella, etc.; Pectinophora agoutipiella, etc.; Phthorimaea spp., etc.; operculella), tomato moth (Tutaabsoluta), etc. of the Gelechiidae family; American white moth (Hyphantria cunea), etc. of the Arctiidae family; sugarcane borer (Telchin licus), etc. of the Castniidae family;Cossidae, including the aromatic wood borer (Cossus insularis); Geometridae, including the large bridge builder (Ascotis selenaria); Limacodidae, including the beautiful green moth (Parasalepida); Stathmopodidae, including the persimmon moth (Stathmopoda masinissa); Sphingidae, including the ghost moth (Acherontia lachesis); Sesiidae, including Nokonaferalis, Synanthedon hector, and Synanthedon tenuis; Hesperiidae, including the straight-striped rice butterfly (Parnara guttata); and Tineidae, including the clothes moth (Tinea translucens) and the curtain moth (Tineola bisselliella).

[0760] Thysanoptera: Thripidae, including Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, and Scirtothrips perseae; and Phlaeothripidae, including Haplothrips aculeatus.

[0761] Diptera: Anthomyiidae, such as Delia platura, Delia antiqua, and Pegomya cunicularia; Ulidiidae, such as Tetanops myopaeformis; Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae, such as Chlorops oryzae; Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, and Bactrocera serrata. oleae), Bactroceratryoni, Ceratitis capitata, Rhagoletis pomonella, Rhacochlaena japonica, etc.; Ephydridae, Hydrellia agriseola, Hydrellia philippina, Hydrelliasasakii, etc.; Drosophilidae, Drosophila suzukii, Drosophilamelanogaster, etc.; Phoridae, Megaselia spiracularis, etc.; Psychodidae, Clogmia albipunctata, etc.; Bradysia edulis, etc. difformis), Bradysia odoriphaga, and other Sciaridae; Mayetiola destructor, Orseolia oryzae, and other Cecidomyiidae; Diopsidae, Diopsis macrophthalma, and other Proboscis eye rope;Glossinidae, including the Central African tsetse fly (Glossina palpalis) and the stinging tsetse fly (Glossina morsitans); Simuliidae, including the Japanese fly (Simulium japonicum) and the hate fly (Simulium damnosum); Phlebotominae; Tipulidae, including the common fly (Tipula aino), the common fly (Tipula oleracea), and the European fly (Tipulapaludosa); Culex pipiens pallens, Culextritae niorhynchus, Culex pipiens f.molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, and Aedes aegypti. aegypti), Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles undaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus, etc.; Simulidae, such as Prosimulium yezoensis and Simulium ornatum; Tabanidae, such as Tabanus trigonus; Musca domestica, Muscina rot fly stabulans), Stomoxys calcitrans, Haematobia irritans, etc., Muscidae; Calliphoridae; Sarcophagidae;Chironomidae, including Chironomus plumosus, Chironomus yoshimatsui, and Glyptotendipes tokunagai; and Fannidae.

[0762] Coleoptera: Diabrotica spp. (e.g., Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Diabrotica barberi, Diabrotica virgiferazeae, Diabrotica balteata, Diabrotica speciosa), Cerotoma trifurcata, Oulemamelanopus, Aulacophora femoralis, Phyllotreta striolata, Phyllotreta cruciferae, Phyllotreta pusilla, Psylliodes chrysocephala), Psylliodes punctulata, Leptinotarsa ​​decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Chaetocnema confinis, Epitrix cucumeris, Dicladispa armigera, Myochrous denticollis, Laccoptera quadrimaculata, Epitrix hirtipennis, Phaedon brassicae, Medythianigrobilineata, etc.; Seedcorn beetle (Stenolophus stenolophus) lecontei), corn seed beetle (Clivina impressifrons), etc. Carabidae;Scarabaeidae species such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophyllapicea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp., Phyllophaga crinita, and other Phyllophaga spp.; Diloboderus abderus and other Argentine beetles; Anthriibidae species such as Araecerus coffeae; and Cylas ant beetles. formicarius; Bruchidae such as the Brazilian bean weevil (Zabrotessubfasciatus); Scolytidae such as the longitudinal pit tip beetle (Tomicus piniperda) and the coffee berry beetle (Hypothenemus hampei); West Indian sweet potato weevil (Euscepespostfasciatus), alfalfa weevil (Hypera postica), corn weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), grain weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), palm weevil (Rhabdoscelus lineaticollis), cotton boll weevil (Anthonomus grandis), parasitic grain weevil (Sphenophorus venatus), southern corn long-beak weevil (Sphenophorus callosus), soybean stem weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), gourd rust weevil (Scepticus griseus), Scepticus uniformis, Aracanthus mourei, etc.; Aracanthus spp., cotton root borer (Eutinobothrus brasiliensis), etc.;Tenebrionidae, such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus; Coccinellidae, such as Epilachna vigintioctopunctata; Bostrychidae, such as Lyctus brunneus and Rhizopertha dominica; Ptinidae; Cerambycidae, such as Anoplophora malasiaca, Migdolus fryanus, and Aromiabungii; Melanotus okinawensis, Agriotes fuscicollis, and Melanotus horned comb beetles. Elateridae, including Elaphes legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., and Aeolus spp.; Staphylinidae, including Paederus fuscipes; Dermestidae, including Anthrenus verbasci, Dermestes maculates, and Trogoderma granarium; Anobiidae, including Lasioderma serricorne and Stegobium paniceum; Cryptolestes spp., including Cryptolestes spp. ferrugineus) and other flat grain beetles (Laemophloeidae); Saw-beetle beetles (Silvanidae) such as the Suriname saw-beetle (Oryzaephilus surinamensis); Nitidulidae such as the rapeseed beetle (Brassicogethesaeneus).

[0763] Orthoptera: Migratory locust (Locusta migratoria), Moroccan halberd locust (Dociostaurus maroccanus), Australian plague locust (Chortoicetes terminifera), Red-winged locust (Nomadacris septemfasciata), Brown migratory locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Long-fronted locust (Melanoplus differentialis), Two-banded grasshopper (Melanoplus bivittatus), Migrant grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged earth locust (Camnula pellucida), Desert locust (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Small-winged rice grasshopper (Oxya The following are some of the family members of the Acrididae family: the Japanese rice locust (Oxya japonica), the Indian yellow-backed locust (Patanga succincta), the African mole cricket (Gryllotalpa orientalis), the Gryllidae family: the house cricket (Acheta domestica), the yellow-faced oil gourd (Teleogryllus emma), and the Tettigoniidae family: the Mormon cricket (Anabrus simplex).

[0764] Hymenoptera: Tenthredinidae, including Athalia rosae and Athalia japonica; Solenopsis spp., including Solenopsis invicta and Solenopsis geminata; Atta spp., including Brown leaf-cutting ants (Attacapiguara); Acromyrmex spp.; Paraponera clavata; Ochetellus glaber; Monomoriumpharaonis; Linepithema humile; Formica japonica; Pristomyrmex punctutus; Pheidole spp. noda), Pheidolemegacephala, Camponotus japonicus, Camponotus obscuripes, and other Camponotus spp., Pogonomyrmex occidentalis, and other Pogonomyrmex spp., Wasmania auropunctata, and other Wasmania spp., and Anoplolepis gracilipes, among others; Vespidae, including the Asian giant hornet (Vespa mandarinia), Vespa simillima, Vespa analis, Vespavelutina, and Polistes jokahamae; and Urocerus occidentalis. gigas) and other tree wasps (Siricidae); Bethylidae.

[0765] Blattodea: German cockroach (Blattella germanica), Ectobiidae; Periplaneta fuliginosa, American cockroach (Periplaneta americana), Australian cockroach (Periplaneta australasiae), Brown cockroach (Periplaneta brunnea), Oriental cockroach (Blattaorientalis), Blattodea; Reticulitermes speratus, Formosan white-spotted termite (Coptotermes formosanus), Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes Termites include the Termitidae, such as the white-necked termite (Glyptotermes satsumensis), the Nakajima termite (Glyptotermes nakajimai), the black tree termite (Glyptotermes fuscus), the forest termite (Hodotermopsis sjostedti), the Guangdong termite (Coptotermes guangzhouensis), the yellow-limbed reticulitermes (Reticulitermes amamianus), the Amami termite (Reticulitermes miyatakei), the closed-door reticulitermes (Reticulitermes kanmonensis), the high mountain elephant termite (Nasutitermes takasagoensis), the Nitobe near-twisted termite (Pericapritermes nitobei), the Taiwan crooked termite (Sinocapritermes mushae), and the corner termite (Cornitermes cumulans).

[0766] Order Siphonaptera: Pulicidae (human flea, Pulex irritans), Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Echidnophaga gallinacea); Hectopsyllidae (Tunga penetrans); Ceratophyllidae (Nosopsyllus fasciatus).

[0767] Psocodae: Pediculidae (human head louse, Pediculus humanus capitis); Pthiridae (pubic louse, Pthirus pubis); Haematopinus usurysternus (cattle blood louse, Haematopinus suis); Linognathidae (calf jaw louse, Linognathus ovillus (sheep jaw louse, Solenopotescapillatus); Bovicoliidae (cattle hair louse, Bovicola bovis (cattle hair louse, Bovicola ovis (sheep hair louse, Bovicola breviceps, Damalinia forficula, Werneckiella spp.); Trichodectes (dog hair louse, Trichodectes) canis), cat louse (Felicola subrostratus), etc.; Menoponidae, such as Menopon gallinae, Menacanthus stramineus, and Trinoton spp.; Trimenoponidae, such as Cummingsia spp.; Trogiidae, such as Trogium pulsatorium; Liposcelidae (or Liposcelididae), such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelisentomophila.

[0768] Thysanura: Lepismatidae such as Ctenolepisma villosa and Lepismasaccharina.

[0769] Acari: Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp., etc. Tetranychidae; Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri), Aceria tosichella, Shevtchenkella sp., etc.; Tarsonemidae, such as Polyphagotarsonemus latus; Tenuipalpidae, such as Brevipalpus phoenicis; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus), Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus; Argasidae, Argas persicus, Ornithodoros hermsi, Ornithodorosturicata; Acaridae, Tyrophagus putrescentiae, Tyrophagus similis; Pyroglyphidae, Dermatophagoides farinae, Dermatophagoides pteronyssinus; Cheyletus eruditus, Cheyletus malaccus, and other carnivorous mites. malaccensis), Chelacaropsis moorei, Cheyletiella yasguri, and other carnivorous mites (Cheyletidae);Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp., etc. of the Psoroptidae family; Notoedres cati, Notoedres muris, Sarcoptes scabiei, etc. of the Sarcoptidae family; Listrophorus gibbus, etc. of the Rabbit family; Dermanyssidae, Dermanyssus gallinae, etc.; Ornithonyssus sylviarum, Ornithonyssus bacoti, etc. of the Macronyssidae family; Varroa varroa, etc. jacobsoni) and other Varroidae; Demodicidae such as Demodex canis and Demodex cati; Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum, and Leptotrombidium scutellare.

[0770] Araneae: Eutichuridae, including the Japanese red-clawed spider (Cheiracanthium japonicum); Theridiidae, including the red-backed spider (Latrodectus hasseltii).

[0771] Polydesmida: Oxidus gracilis, Nedyopustambanus, etc. Paradoxosomatidae.

[0772] Isopoda: Common beetle (Armadillidium vulgare), etc. Armadillidiidae.

[0773] Class Chilopoda: Scutigeridae, including Thereuonema hilgendorfi; Scolopendridae, including Scolopendra subspinipes; and Ethopolyidae, including Bothropolys rugosus.

[0774] Gastropoda: Limacidae, such as Limax marginatus and Limaxflavus; Philomycidae, such as Meghimatium bilineatum; Ampullariidae, such as Pomacea canaliculata; Lymnaeidae, such as Austropeplea ollula.

[0775] Nematodes: Aphelenchoididae, including the rice stem-tipped nematode Aphelenchoides besseyi; Pratylenchidae, including the coffee short-bodied nematode Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, and Radopholus similis; Java root-knot nematodes Meloidogyne javanica, southern root-knot nematodes Meloidogyne incognita, guava root-knot nematodes Meloidogyne enterolobii, northern root-knot nematodes Meloidogyne hapla, soybean cyst nematodes Heterodera glycines, and potato golden nematodes Globodera spp. Heteroderidae, such as Potato white nematode (Globodera pallida), and Columbia root-knot nematode (Meloidogyne chitwoodi); Hoplolaimidae, such as Rotylenchulus reniformis; Anguinidae, such as Nothotylenchus acris and Ditylenchus dipsaci; Tylenchulidae, such as Tylenchulus semipenetrans; Longidoridae, such as Xiphinema index; Trichodoridae; and Parasitaphelenchidae, such as Bursaphelenchus xylophilus.

[0776] Harmful insects, harmful mites, and other harmful arthropods, harmful mollusks, and harmful nematodes may be those whose sensitivity to insecticides, acaricides, molluscicides, or nematodes is reduced, or those that are highly resistant to them.

[0777] The method for controlling harmful arthropods of the present invention can be implemented by directly applying an effective amount of the compound of the present invention or composition A to harmful arthropods and / or applying it to the habitats of harmful arthropods (plants, soil, houses, animals, etc.). Examples of the method for controlling harmful arthropods of the present invention include foliage treatment, soil treatment, root treatment, spraying treatment, fumigation treatment, water surface treatment, and seed treatment.

[0778] For the compound or composition A of the present invention, an inactive carrier such as a solid carrier, a liquid carrier, a gaseous carrier and a surfactant are usually mixed, and as needed, a binder, a dispersant, a stabilizer and other formulation adjuvants are further added to formulate them into aqueous suspension preparations, oily suspension preparations, oil preparations, emulsions, emulsion preparations, microemulsion preparations, microcapsule preparations, wettable powders, water-dispersible granules, powders, granules, tablets, aerosol preparations, resin preparations and the like for use. The present invention is not limited to these preparations, and can be formulated into the dosage forms described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271-276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications (Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271-276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications), 2016, ISSN: 0259-2517 for use.

[0779] These preparations usually contain 0.0001 to 99% of the compound or composition A of the present invention by weight.

[0780] Examples of the solid support include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0781] Examples of the liquid carrier include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0782] Examples of the gaseous support include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0783] Examples of the surfactant include nonionic surfactants (polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, etc.) and anionic surfactants (alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, etc.).

[0784] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, and the like. Specifically, they include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and butylated hydroxytoluene.

[0785] In addition, adjuvants can be used as components that enhance or assist the efficacy of the compounds of the present invention. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0786] In the present invention, examples of the plant include the whole plant, stems and leaves, flowers, ears, fruits, trunks, branches, crowns, seeds, vegetative propagation organs, and seedlings.

[0787] Vegetative propagation organ refers to: among the root, stem, leaf etc. of plant, the position with the ability of growing when this position is cut off from main body and is arranged in soil.As vegetative propagation organ, can enumerate for example tuberous root (tuberous root), creeping root (creeping root), bulb (bulb), corm (corm or solid bulb), tuber (tuber), rhizome (rhizome), stolon (stolon), rhizophore (rhizophore), stem cuttings (cane cuttings), propagation bud (propagule) and vine cuttings (vine cutting).It should be noted that stolon is sometimes also referred to as runner (runner), and propagation bud is also referred to as bulbil, is divided into fleshy bud (broad bud) and bulbil (bulbil).Vine cuttings refer to the slender (general term of leaf and stem, rootless seedling (shoot)) of sweet potato, Japanese yam etc. The term "bulb" also refers to bulbs, corms, tubers, rhizomes, stem cuttings, root tubers, or tubers. Tuber cultivation begins by planting tubers in the soil, but the tubers used are usually called seed potatoes.

[0788] As a method for controlling harmful arthropods by applying an effective amount of the compound or composition A of the present invention to the soil, for example, a method of applying an effective amount of the compound or composition A of the present invention to the soil before or after transplanting plants. More specifically, for example, hole treatment (hole spreading, hole treatment soil mixing), root treatment (root spreading, root soil mixing, root irrigation, root treatment in the late seedling stage), furrow treatment (furrow spreading, furrow soil mixing), furrow treatment (furrow spreading, furrow soil mixing, furrow spreading during the growing period), furrow treatment at sowing (furrow spreading at sowing, furrow soil mixing at sowing), comprehensive treatment (whole soil spreading, whole soil mixing), ridge side treatment, water surface treatment (water surface application, water surface application after water storage), other soil spreading treatments (leaf spreading of granules during the growing period, spreading under the canopy or around the trunk, soil surface spreading, soil surface mixing, hole spreading, ridge ground surface scattering, inter-plant scattering), other irrigation treatments (soil irrigation, irrigation during the seedling period, liquid injection treatment, irrigation at the base of the plant, liquid drip irrigation, chemical solution irrigation), seedling box treatment (seedling box scattering, seedling box irrigation, seedling box liquid accumulation), seedling tray treatment (seedling tray scattering, seedling tray irrigation, seedling tray liquid accumulation), seedling bed treatment (seedling bed scattering, seedling bed irrigation, nursery bed scattering, seedling soaking), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, scattering before covering soil at sowing, scattering after covering soil at sowing, covering soil mixing), and other treatments (cultivated soil mixing, turning in, topsoil mixing, rainwater drip soil mixing, planting position treatment, granular calyx scattering, paste fertilizer mixing).

[0789] Examples of seed treatment include treatments of seeds or vegetative propagation organs with the compound or composition A of the present invention. Specifically, examples include: spraying treatments in which a suspension of the compound or composition A of the present invention is atomized and sprayed onto the surface of seeds or vegetative propagation organs; coating treatments in which the compound or composition A of the present invention is applied to seeds or vegetative propagation organs; immersion treatments in which seeds or vegetative propagation organs are immersed in a solution of the compound or composition A of the present invention for a predetermined period of time; and methods in which seeds or vegetative propagation organs are coated with a carrier containing the compound or composition A (coating treatments, pellet coating treatments, etc.). Examples of the vegetative propagation organs include seed potatoes.

[0790] When treating seeds or vegetative propagation organs with composition A, composition A may be prepared as a single formulation for treating the seeds or vegetative propagation organs, or composition A may be prepared as multiple different formulations for treating the seeds or vegetative propagation organs in multiple batches. Examples of methods for treating the seeds or vegetative propagation organs with multiple different formulations include: treating the seeds or vegetative propagation organs with a formulation containing only the compound of the present invention as an active ingredient, allowing the seeds or vegetative propagation organs to air-dry, and then treating the seeds or vegetative propagation organs with a formulation containing the present ingredient; and treating the seeds or vegetative propagation organs with a formulation containing the compound of the present invention and the present ingredient as active ingredients, allowing the seeds or vegetative propagation organs to air-dry, and then treating the seeds or vegetative propagation organs with a formulation containing the present ingredient other than the treated present ingredient.

[0791] The seeds or vegetative propagation organs retaining the compound or composition A of the present invention in the present invention refer to seeds or vegetative propagation organs in a state where the compound or composition A of the present invention is attached to the surface of the seeds or vegetative propagation organs. For the seeds or vegetative propagation organs retaining the compound or composition A of the present invention, materials other than the compound or composition A of the present invention may be attached before or after the compound or composition A of the present invention is attached to the seeds or vegetative propagation organs.

[0792] In addition, when composition A forms a layer on the surface of a seed or a vegetative propagation organ and adheres to it, the layer is formed by one layer or multiple layers. In addition, when formed by multiple layers, each layer is a layer containing one or more active ingredients, or is formed by a layer containing one or more active ingredients and a layer not containing an active ingredient.

[0793] Seeds or vegetative propagation organs containing the compound or composition A of the present invention can be obtained, for example, by applying a formulation containing the compound or composition A of the present invention to seeds or vegetative propagation organs using the aforementioned seed treatment method.

[0794] When the compound or composition A of the present invention is used for controlling harmful arthropods in agricultural fields, the application rate is: 2 The amount of the compound of the present invention is usually 1 to 10,000 g. When treating seeds or vegetative propagation organs, the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g per kg of seeds or vegetative propagation organs. When the compound of the present invention or composition A is formulated into an emulsion, wettable powder, suspension, etc., it is usually diluted with water to a concentration of 0.01 to 10,000 ppm of the active ingredient and applied. Granules, powders, etc. are usually applied directly.

[0795] Alternatively, the compound or composition A of the present invention can be treated by winding a resin preparation processed into a sheet or string around crops, stretching it near crops, or laying it on the soil around the roots.

[0796] When the compound or composition A of the present invention is used to control harmful arthropods that inhabit houses, the application rate is, when treating on the surface, 1m 2 The amount of the compound of the present invention per treatment area is usually 0.01 to 1000 mg. When the treatment is carried out in space, the amount is per 1 m 3 The amount of the compound of the present invention applied to the treated space is generally 0.01 to 500 mg. When the compound of the present invention or composition A is formulated into an emulsion, wettable powder, suspension, or the like, it is usually diluted with water to a concentration of 0.1 to 10,000 ppm of the active ingredient and applied directly. Alternatively, an oil formulation, aerosol formulation, fumigant, or poison bait formulation may be used.

[0797] The compounds of this invention or composition A are used to prevent and treat external parasites of small animals such as cattle, horses, pigs, sheep, goats, chickens, dogs, cats, rats, mice, etc., and can be used for animals by methods known in veterinary medicine. As a specific method of use, in the case of systemic suppression for the purpose, by, for example, tablets, feeds mixed in, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) to apply, in the case of non-systemic suppression for the purpose, by, for example, oils or aqueous liquids are sprayed, poured or sprayed, shampoo formulations are used to wash animals, or resin formulations are made into collars, ear tags and animals are worn. The amount of the compounds of this invention or composition A when applied to animals is generally in the range of 0.1 to 1000 mg relative to the body weight 1 kg of the animal.

[0798] The compound or composition A of the present invention can be used as an agent for controlling harmful arthropods in agricultural lands such as dry fields, paddy fields, lawns, and orchards. Examples of plants include the following.

[0799] Corn (dent, hard, soft, popping, glutinous, sweet, and non-sweet corn), rice (long-grain, short-grain, medium-grain, Japonica, tropical Japonica, Indica, Javanese, upland rice, floating rice, direct-seeded, transplanted, and glutinous rice), wheat (bread wheat (hard, soft, medium, red, and white), durum wheat, spelt, and club wheat, as well as various winter and spring wheat types), barley (two-row barley (= malting barley), six-row barley, naked barley, and various sticky barley types), (winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, Pima type), soybeans (mature seed harvest varieties, branch bean varieties, green cutting varieties, each indeterminate growth type, determinate growth type, semi-determinate growth type), peanuts, buckwheat, sugar beets (for sugar production, feed, root vegetables, leafy vegetables, fuel), rapeseed (winter rapeseed type, spring rapeseed type), Canadian rapeseed (winter Canadian rapeseed type, spring Canadian rapeseed type), sunflower (for oil extraction, food Vegetables for ornamental purposes (e.g., eggplant, tomato, green pepper, hot pepper, potato), cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower), Asteraceae vegetables (burdock, chamomile, artichoke, lettuce), Liliaceae vegetables (scallion, onion, garlic, asparagus), Umbelliferae vegetables (carrot, parsley, celery, parsnip), Chenopodiaceae vegetables (spinach, pachyderm), Lamiaceae vegetables (perilla, mint), , basil, etc.), strawberry, sweet potato, Japanese yam, taro, pome fruit (apple, pear, Japanese pear, white pear, papaya crabapple, quince, etc.), stone fruit (peach, plum, nectarine, greengage, cherry, apricot, prune, etc.), citrus (Wenzhou mandarin orange, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew, macadamia, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, fig, olive, loquat, banana, coffee, date, coconut, ornamental plants, forest plants, lawn grass, forage grass.

[0800] The above-mentioned plants are not particularly limited as long as they are commonly cultivated varieties. The above-mentioned plants also include plants that can be made by natural mating, plants that can be produced by mutation, F1 hybrid plants and genetically modified crops. As genetically modified crops, for example, plants that are endowed with resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr, thifensulfuron, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil or dicamba; plants that can synthesize selective toxins known in Bacillus thuringiensis such as Bacillus thuringiensis; plants that can be endowed with specific insecticidal activity by synthesizing gene fragments that are partially identical to endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insects.

[0801] Example

[0802] Hereinafter, the present invention will be described in more detail using production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.

[0803] In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, t-Bu represents a tert-butyl group, C2F5 represents a perfluoroethyl group, c-Pr represents a cyclopropyl group, CF3 represents a trifluoromethyl group, CF2H represents a difluoromethyl group, Ph represents a phenyl group, Py2 represents a 2-pyridyl group, Py3 represents a 3-pyridyl group, and Py4 represents a 4-pyridyl group. When c-Pr, Ph, Py2, Py3, and Py4 have a substituent, the substitution position is described together before the substituent symbol. For example, 1-CN-c-Pr represents 1-cyanocyclopropyl, 3,4-F2-Ph represents 3,4-difluorophenyl, 2-C2F5-Ph represents 2-(perfluoroethyl)phenyl, 4-SO2CF3-Ph represents 4-(trifluoromethanesulfonyl)phenyl, 3,4-(OCF3)2-Ph represents 3,4-bis(trifluoromethoxy)phenyl, 3-SCF3-4-OCF3-Ph represents 3-[(trifluoromethyl)thio]-4-(trifluoromethoxy)benzene yl, 4-CF3-Py2 represents 4-(trifluoromethyl)-2-pyridyl, 3-CF2H-1-i-Pr-1H-pyrrol-2-yl represents 3-difluoromethyl-1-isopropyl-2-1H-pyrrolyl, 4-CF2H-1-Me-1H-imidazol-2-yl represents 4-difluoromethyl-1-methyl-2-1H-imidazol-2-yl, and 3-CF2H-1-Me-1H-pyrazol-5-yl represents 3-difluoromethyl-1-methyl-5-1H-pyrazolyl.

[0804] First, production examples of the compound of the present invention and its production intermediates are shown.

[0805] When the physical properties of the compound were measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] was recorded. + or [MH] - The conditions for liquid chromatography (hereinafter referred to as LC) are as follows.

[0806] [LC conditions]

[0807] Column: L-column2 ODS, inner diameter 4.6mm, length 30mm, particle size 3μm (National Institute for the Evaluation of Chemical Substances)

[0808] UV measurement wavelength: 254nm

[0809] Mobile phase: Solution A: 0.1% formic acid in water, Solution B: 0.1% formic acid in acetonitrile

[0810] Flow rate: 2.0 mL / min

[0811] Gradient conditions: Liquid was delivered using the concentration gradient described in [Table LC1].

[0812] [Table 1]

[0813] [Table LC1]

[0814] Time (min) Liquid A (%) Liquid B (%) 0.01 90 10 2.00 0 100 4.0 0 0 10 0 4.0 1 90 10

[0815] Reference Production Example 1

[0816] To a mixture of 0.7 g of 5-methylisoxazole-5-carboxylic acid and 10 mL of pyridine were added 1.6 g of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1.5 g of 6-iodo-3-(ethylthio)imidazo[1,2-a]pyridin-2-amine (hereinafter referred to as Intermediate Z), produced by the method described in International Publication No. 2018 / 052136. The mixture was stirred at 80°C for 4 hours. Water was added to the resulting mixture, and the precipitated solid was filtered and dried to obtain 1.8 g of Intermediate 1 represented by the following formula.

[0817] [Chemical Formula 28]

[0818]

[0819] Intermediate 1: 1H-NMR (CDCl3): 8.73 (1H, br s), 8.64-8.63 (1H, m), 7.54-7.51 (1H, m), 7.49-7.47 (1H, m), 7.32 (1H, s), 6.86 (1H, t), 2.75 (2H, q), 1.25 (3H, t).

[0820] Reference Production Example 1-1

[0821] The compounds produced according to Reference Production Example 1 and their physical properties are shown below.

[0822] In the compound represented by formula (A-1), Z 1 、X 1 、X 2 、X 3 , G 2 and G 3 The combination is any combination of compounds described in [Table A-1].

[0823] [Chemical Formula 29]

[0824]

[0825] [Table 2]

[0826] [Table A-1]

[0827] Intermediate <![CDATA[Z 1 ]]> <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 2 ]]> <![CDATA[G 2 ]]> <![CDATA[G 3 ]]> 2 N-Me CH CH N C-I CH 3 N-Me CH <![CDATA[C-CF3]]> N C-I CH 4 <![CDATA[N-CF2H]]> CH CH N C-I CH 5 O CH CH <![CDATA[C-CF3]]> C-I CH 6 S CH CH <![CDATA[C-CF3]]> C-I CH 7 S CH N <![CDATA[C-CF3]]> C-I CH 8 S CH N <![CDATA[C-CF3]]> C-Br CH 9 S CH N <![CDATA[C-CF3]]> <![CDATA[C-CF3]]> CH 10 S CH N <![CDATA[C-CF3]]> CH C-I 11 S CH N <![CDATA[C-CF3]]> CH C-Br 12 S CH N C-CI C-I CH 13 S N <![CDATA[C-CF3]]> CH C-I CH

[0828] Intermediate 2: 1 H-NMR (CDCl3) δ: 8.62-8.61 (1H, m), 8.19 (1H, br s), 7.54 (1H, d), 7.53-7.46 (2H, m), 6.73 (1H, d), 4.27 (3H, s), 2.72 (2H, q), 1.24 (3H, t).

[0829] Intermediate 3: 1 H-NMR (CDCl3) δ: 8.62-8.61 (1H, m), 8.25 (1H, brs), 7.51-7.49 (2H, m), 6.97 (1H, s), 4.31 (3H, s), 2.73 (2H, q), 1.25-1.23 (3H, m).

[0830] Intermediate 4: LCMS: 464 [M+H]+, RT = 1.79 min

[0831] Intermediate 5: 1H-NMR (CDCl3) δ: 8.64-8.63 (1H, m), 8.56 (1H, br s), 7.52-7.49(1H, m), 7.46-7.44(1H, m), 7.36-7.35(1H, m), 6.98-6.97(1H, m), 2.76(2H, q), 1.25(3H, t).

[0832] Intermediate 6: LCMS: 498 [M+H]+, RT = 2.06 min

[0833] Intermediate 7: 1 H-NMR (CDCl3) δ: 8.64-8.64 (1H, m), 8.41-8.41 (1H, m), 8.31 (1H, br s), 7.54-7.52 (1H, m), 7.45-7.43 (1H, m), 2.76 (2H, q), 1.24 (3H, t).

[0834] Intermediate 8: 1 H-NMR (CDCl3) δ: 8.54-8.54 (2H, m), 8.44-8.44 (1H, m), 7.54 (1H, dd), 7.41 (1H, dd), 2.77 (2H, q), 1.24 (3H, t).

[0835] Intermediate 9: 1 H-NMR (CDCl3) δ: 8.77-8.76 (1H, m), 8.47 (1H, br s), 8.45-8.44 (1H, m), 7.76 (1H, d), 7.50 (1H, dd), 2.80 (2H, q), 1.26 (3H, t).

[0836] Intermediate 10: LCMS: 499 [M+H] +, RT = 1.91 min

[0837] Intermediate 11: LCMS: 451 [M+H]+, RT = 1.86 min

[0838] Intermediate 12: LCMS: 465 [M+H]+, RT = 1.83 minutes

[0839] Intermediate 13: 1 H-NMR(CDCl3)δ:9.53(1H,br s),8.64-8.64(1H,m),8.07-8.07(1H,m),7.53-7.50(1H,m),7.49-7.46(1H,m),2.75(2H,q),1.25(3H,t).

[0840] Reference Manufacturing Example 1-2

[0841] The compounds produced according to Reference Production Example 1 and their physical properties are shown below.

[0842] In the compound represented by formula (A-2), Z 2 、X 1 、X 2 、X 4 , G 2 and G 3 The combination is any combination of compounds described in [Table A-2].

[0843] [Chemical formula 30]

[0844]

[0845] [Table 3]

[0846] [Table A-2]

[0847] Intermediate <![CDATA[Z 2 ]]> <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 4 ]]> <![CDATA[G 2 ]]> <![CDATA[G 3 ]]> 14 N-Me <![CDATA[C-CF3]]> N CH C-I CH 15 N-Me <![CDATA[C-CF2H]]> N CH C-Br CH 16 N-Me CH <![CDATA[C-CF3]]> N C-I CH 17 N-Me CH C-Br N C-I CH 18 N-Me CH <![CDATA[C-OCF2H]]> N C-I CH 19 <![CDATA[N-CF2H]]> CH CH N C-I CH 20 N-c-Pr CH CH N C-I CH 21 <![CDATA[N-CH2CF3]]> CH CH N C-I CH 22 <![CDATA[N-CF2H]]> CH C-Me N C-I CH 23 <![CDATA[N-CF3]]> CH N CH C-I CH 24 <![CDATA[N-CF2H]]> CH N CH C-I CH 25 N-c-Pr CH N CH C-I CH 26 N-Me CH N <![CDATA[C-CF3]]> C-I CH 27 <![CDATA[N-CH2CF3]]> N N CH C-I CH 28 N-Me <![CDATA[C-CF3]]> CH CH C-I CH 29 O CH <![CDATA[C-CF3]]> N C-I CH 30 O CH C-i-Pr N C-I CH 31 O CH C-i-Pr N C-Br CH 32 O CH C-i-Pr N <![CDATA[C-CF3]]> CH 33 O CH C-i-Pr N CH C-I 34 O CH C-i-Pr N CH C-Br

[0848] Intermediate 14: 1 H-NMR (CDCl3) δ: 8.60-8.60 (1H, m), 8.29 (1H, br s), 8.12 (1H, s), 7.47-7.46 (2H, m), 4.01 (3H, s), 2.70 (2H, q), 1.20 (3H, t).

[0849] Intermediate 15: 1 H-NMR (CDCl3) δ: 8.59 (1H, br s), 8.51-8.50 (1H, m), 8.10 (1H, s), 7.56 (1H, d), 7.35 (1H, dd), 6.93 (1H, t), 3.98 (3H, s), 2.70 (2H, q), 1.21 (3H, t).

[0850] Intermediate 16: LCMS: 496 [M+H]+, RT = 1.95 min

[0851] Intermediate 17: 1 H-NMR (CDCl3) δ: 9.13 (1H, br s), 8.61-8.60 (1H, m), 7.46-7.45 (2H, m), 6.99 (1H, s), 3.97 (3H, s), 2.71 (2H, q), 1.22 (3H, t).

[0852] Intermediate 18: LCMS: 494 [M+H]+, RT = 1.85 min

[0853] Intermediate 19: LCMS: 464 [M+H]+, RT = 1.69 min

[0854] Intermediate 20: LCMS: 454 [M+H]+, RT = 1.70 min

[0855] Intermediate 21: LCMS: 496 [M+H] +, RT = 1.83 minutes

[0856] Intermediate 22: LCMS: 478 [M+H]+, RT = 1.86 min

[0857] Intermediate 23: 1 H-NMR(CDCl3)δ:8.63-8.63(1H,m),8.47(1H,s),8.19(1H,br s),8.15(1H,s),7.52-7.49(1H,m),7.42(1H,d),2.74(2H,q),1.23(3H,t).

[0858] Intermediate 24: LCMS: 464 [M+H]+, RT = 1.63 min

[0859] Intermediate 25: LCMS: 454 [M+H]+, RT = 1.55 min

[0860] Intermediate 26: LCMS: 496 [M+H] +, RT = 1.75 min

[0861] Intermediate 27: LCMS: 497 [M+H]+, RT = 1.79 min

[0862] Intermediate 28: LCMS: 495 [M+H]+, RT = 1.69 min

[0863] Intermediate 29: LCMS: 483 [M+H]+, RT = 2.02 minutes

[0864] Intermediate 30: LCMS: 457 [M+H]+, RT = 1.96 min

[0865] Intermediate 31: LCMS: 409 [M+H]+, RT = 1.93 min

[0866] Intermediate 32: LCMS: 399 [M+H] +, RT = 1.98 minutes

[0867] Intermediate 33: LCMS: 457 [M+H]+, RT = 1.94 min

[0868] Intermediate 34: LCMS: 409 [M+H]+, RT = 1.90 min

[0869] Production Example 1

[0870] To a mixture of 1.2g of intermediate 1, cesium carbonate 2.4g and DMF 5mL, iodomethane 0.31mL was added under ice-cooling conditions and stirred at room temperature for 5 hours. Water was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was dried using anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 1.1g of compound 1 of the present invention.

[0871] [Chemical Formula 31]

[0872]

[0873] Compound 1 of the present invention: 1 H-NMR(CDCl3)δ:8.60-8.59(1H,m),7.56-7.53(1H,m),7.39-7.36(1H,m) ,6.75-6.56(1H,m),6.65(1H,t),3.56(3H,s),2.59(2H,q),1.17(3H,t).

[0874] Production Example 1-1

[0875] The compounds produced according to Production Example 1 and their physical properties are shown below.

[0876] In the compound represented by formula (B-1), n, Z 1 、X 1 、X 2 、X 3 , G 2 , G 3 and R 1 The combination is any combination of compounds listed in [Table B-1]

[0877] [Chemical Formula 32]

[0878]

[0879] [Table 4]

[0880] [Table B-1]

[0881]

[0882] Compound 2 of the present invention: 1 H-NMR(CDCl3)δ:8.46(1H,s),7.53(1H,d),7.41(1H,d),7.08(1H,s),5.63(1H,s),4.16(3H,s),3.51(3H,s),2.37(2H,q),1.13(3H,t).

[0883] Compound 3 of the present invention:1 H-NMR(CDCl3)δ:8.49-8.48(1H,m),7.57-7.55(1H,m),7.43-7.40(1H,m),5.93(1H,s),4.19(3H,s),3.52(3H,s),2.46(2H,q),1.14(3H,t).

[0884] Compound 4 of the present invention: 1 H-NMR(CDCl3)δ:8.48-8.48(1H,m),7.92(1H,t),7.56(1H,dd),7.43(1H,dd),7.37(1H,s),5.74(1H,s),3.51(3H,s),2.40(2H,q),1.12(3H,t).

[0885] Compound 5 of the present invention: 1 H-NMR(CDCl3)δ:8.60-8.60(1H,m),7.54-7.52(1H,m),7.38-7.36(1H,m),6 .66-6.62(1H,m),6.66-6.66(1H,m),3.53(3H,s),2.54(2H,q),1.15(3H,t).

[0886] Compound 6 of the present invention: 1 H-NMR(CDCl3)δ:8.56-8.55(1H,m),7.59-7.56(1H,m),7.46-7.43(1H,m),7 .08-7.06(1H,m),6.79-6.77(1H,m),3.50(3H,s),2.46(2H,q),1.12(3H,t).

[0887] Compound 7 of the present invention: 1 H-NMR(CDCl3)δ:8.57-8.56(1H,m),7.61-7.58(1H,m),7.50-7.50(1H,m),7.46-7.43(1H,m),3.53(3H,s),2.55(2H,q),1.15(3H,t).

[0888] Compound 8 of the present invention: 1 H-NMR(CDCl3)δ:8.47-8.46(1H,m),7.56(1H,dd),7.51(1H,d),7.49(1H,dd),3.53(3H,s),2.55(2H,q),1.15(3H,t).

[0889] Compound 9 of the present invention: 1H-NMR(CDCl3)δ:8.69-8.68(1H,m),7.77(1H,d),7.57(1H,dd),7.49-7.49(1H,m),3.55(3H,s),2.58(2H,q),1.16(3H,t).

[0890] Compound 10 of the present invention: LCMS: 513 [M+H]+, RT=2.02 minutes

[0891] Compound 11 of the present invention: 1 H-NMR(CDCl3)δ:8.21(1H,dd),7.85(1H,dd),7.54-7.53(1H,m),7.15(1H,dd),3.52(3H,s),2.53(2H,q),1.13(3H,t).

[0892] Compound 12 of the present invention: 1 H-NMR(CDCl3)δ:8.59-8.59(1H,m),7.61-7.58(1H,m),7.46-7.43(1H,m),7.35(1H,s),3.48(3H,s),2.57(2H,q),1.16(3H,t).

[0893] Compound 13 of the present invention: 1 H-NMR(CDCl3)δ:8.63-8.62(1H,m),7.78(1H,s),7.51-7.48(1H,m),7.33-7.31(1H,m),3.62(3H,s),2.63(2H,q),1.17(3H,t).

[0894] Production Example 1-2

[0895] The compounds produced according to Production Example 1 and their physical properties are shown below.

[0896] In the compound represented by formula (B-2), n, Z 2 、X 1 、X 2 、X 4 , G 2 , G 3 and R 1 The combination is any combination of compounds listed in [Table B-2]

[0897] [Chemical Formula 33]

[0898]

[0899] [Table 5]

[0900] [Table B-2]

[0901]

[0902] Compound 14 of the present invention: 1 H-NMR(CDCl3)δ:8.53-8.52(1H,m),7.55-7.53(1H,m),7.42-7.39(1H,m),7.05(1H,s),3.71(3H,s),3.46(3H,s),2.52(2H,q),1.13(3H,t).

[0903] Compound 15 of the present invention: 1 H-NMR(CDCl3)δ:8.45-8.45(1H,m),7.55(1H,d),7.45(1H,dd),7.21(1H,t),6.77(1H,s),3.69(3H,s),3.45(3H,s),2.48(2H,q),1.11(3H,t).

[0904] Compound 16 of the present invention: 1 H-NMR(CDCl3)δ:8.57-8.57(1H,m),7.52-7.49(1H,m),7.41-7.38(1H,m),6.74(1H,s),3.74(3H,s),3.54(3H,s),2.53(2H,q),1.13(3H,t).

[0905] Compound 17 of the present invention: 1 H-NMR(CDCl3)δ:8.57-8.57(1H,m),7.50(1H,dd),7.40(1H,d),6.26(1H,s),3.67(3H,s),3.52(3H,s),2.52(2H,q),1.12(3H,t).

[0906] Compound 18 of the present invention: 1 H-NMR(CDCl3)δ:8.57-8.56(1H,m),7.49(1H,dd),7.39(1H,dd),6.37(1H,t),5.93(1H,s),3.52(3H,s),3.51(3H,s),2.52(2H,q),1.12(3H,t).

[0907] Compound 19 of the present invention: 1H-NMR(CDCl3)δ:8.54-8.54(1H,m),7.58(1H,d),7.52-7.50(1H,m),7.40-7. 38(1H,m),6.92(1H,t),6.43(1H,s),3.55(3H,s),2.47(2H,q),1.11(3H,t).

[0908] Compound 20 of the present invention: LCMS: 468 [M+H]+, RT=1.67 minutes

[0909] Compound 21 of the present invention: 1 H-NMR(CDCl3)δ:8.53-8.52(1H,m),7.49(1H,dd),7.37(1H,dd),7.27(1H, s),6.49-6.49(1H,m),4.44(2H,q),3.54(3H,s),2.45(2H,q),1.11(3H,t).

[0910] Compound 22 of the present invention: LCMS: 492 [M+H]+, RT = 1.77 minutes

[0911] Compound 23 of the present invention: 1 H-NMR(CDCl3)δ:8.56-8.55(1H,m),8.01(1H,s),7.59-7.56(1H,m),7.45-7.42(1H,m),7.00(1H,s),3.48(3H,s),2.51(2H,q),1.12(3H,t).

[0912] Compound 24 of the present invention: 1 H-NMR(CDCl3)δ:8.55-8.55(1H,m),7.93(1H,s),7.58-7.55(1H,m),7.45-7. 43(1H,m),7.02(1H,t),6.99(1H,s),3.48(3H,s),2.47(2H,q),1.10(3H,t).

[0913] Compound 25 of the present invention: LCMS: 468 [M+H]+, RT=1.69 minutes

[0914] Compound 26 of the present invention: 1 H-NMR(CDCl3)δ:8.47-8.47(1H,m),7.50(1H,dd),7.37(1H,dd),7.03(1H,s),3.89(3H,s),3.50(3H,s),2.56(2H,q),1.15(3H,t).

[0915] Compound 27 of the present invention: 1 H-NMR(CDCl3)δ:8.58-8.58(1H,m),8.10(1H,s),7.50-7.47(1H,m),7.37-7.34(1H,m),4.88(2H,q),3.58(3H,s),2.56(2H,q),1.15(3H,t).

[0916] Compound 28 of the present invention: 1 H-NMR(CDCl3)δ:8.53-8.52(1H,m),7.51(1H,dd),7.40(1H,dd),6.79-6.7 9(1H,m),6.25(1H,d),3.44(3H,s),3.39(3H,s),2.45(2H,q),1.10(3H,t).

[0917] Compound 29 of the present invention: 1 H-NMR(CDCl3)δ:8.59-8.59(1H,m),7.53-7.51(1H,m),7.36-7.34(1H,m),7.04(1H,s),3.58(3H,s),2.66(2H,q),1.22-1.17(3H,m).

[0918] Compound 30 of the present invention: 1 H-NMR(CDCl3)δ:8.58-8.57(1H,m),7.48(1H,dd),7.36(1H,dd),6.29(1H,s), 3.55(3H,s),3.01-2.94(1H,m),2.60(2H,q),1.28-1.20(6H,m),1.17(3H,t).

[0919] Compound 31 of the present invention: 1 H-NMR(CDCl3)δ:8.48-8.47(1H,m),7.47(1H,dd),7.37(1H,dd),6.29(1H,s), 3.55(3H,s),3.01-2.94(1H,m),2.60(2H,q),1.26-1.22(6H,m),1.17(3H,t).

[0920] Compound 32 of the present invention: LCMS: 413 [M+H]+, RT=1.96 minutes

[0921] Compound 33 of the present invention: 1H-NMR(CDCl3)δ:8.09(1H,d),7.97-7.97(1H,m),7.19(1H,dd),6.28(1H,s),3.5 4(3H,s),3.01-2.92(1H,m),2.60-2.54(2H,m),1.24-1.18(6H,m),1.15(3H,t).

[0922] Compound 34 of the present invention: LCMS: 423 [M+H]+, RT = 1.90 minutes

[0923] Production Example 2

[0924] To a mixture of 0.87g of the compound of the present invention 1 and 10mL of chloroform, 1.5g of mCPBA (purity of 65%, containing 35% water) was added under ice-cooling conditions and stirred at room temperature for 2 hours. Saturated aqueous sodium bicarbonate solution and aqueous sodium thiosulfate solution were added sequentially to the obtained mixture, stirred at room temperature for 3 hours, and then extracted with chloroform. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.76g of compound of the present invention 35.

[0925] [Chemical Formula 34]

[0926]

[0927] Compound 35 of the present invention: LCMS: 511 [M+H]+, RT=1.73 minutes

[0928] Production Example 2-1

[0929] The compounds produced according to Production Example 2 and their physical properties are shown below.

[0930] In the compound represented by formula (B-3), n, Z 1 、X 1 、X 2 、X 3 , G 2 , G 3 and R 1 The combination is any combination of compounds listed in [Table B-3]

[0931] [Chemical Formula 35]

[0932]

[0933] [Table 6]

[0934] [Table B-3]

[0935]

[0936] Compound 36 of the present invention: LCMS: 542 [M+H]+, RT=1.87 minutes

[0937] Compound 37 of the present invention: LCMS: 494 [M+H]+, RT = 1.44 minutes

[0938] Compound 38 of the present invention: LCMS: 510 [M+H]+, RT=1.61 minutes

[0939] Compound 39 of the present invention: LCMS: 528 [M+H]+, RT = 1.83 minutes

[0940] Compound 40 of the present invention: LCMS: 545 [M+H]+, RT=1.80 min

[0941] Compound 41 of the present invention: LCMS: 481 [M+H]+, RT=1.71 minutes

[0942] Compound 42 of the present invention: LCMS: 497 [M+H]+, RT=1.77 minutes

[0943] Compound 43 of the present invention: LCMS: 471 [M+H]+, RT=1.81 minutes

[0944] Compound 44 of the present invention: LCMS: 487 [M+H]+, RT=1.85 minutes

[0945] Compound 45 of the present invention: LCMS: 529 [M+H]+, RT = 1.76 minutes

[0946] Compound 46 of the present invention: LCMS: 545 [M+H]+, RT=1.82 minutes

[0947] Compound 47 of the present invention: LCMS: 481 [M+H]+, RT=1.73 minutes

[0948] Compound 48 of the present invention: LCMS: 497 [M+H]+, RT=1.79 minutes

[0949] Compound 49 of the present invention: LCMS: 511 [M+H]+, RT = 1.73 minutes

[0950] Compound 50 of the present invention: LCMS: 545 [M+H]+, RT=1.79 minutes

[0951] Production Example 2-2

[0952] The compounds produced according to Production Example 2 and their physical properties are shown below.

[0953] In the compound represented by formula (B-4), n, Z2 、X 1 、X 2 、X 4 , G 2 , G 3 and R 1 The combination is any combination of compounds listed in [Table B-4]

[0954] [Chemical Formula 36]

[0955]

[0956] [Table 7]

[0957] [Table B-4]

[0958]

[0959] Compound 51 of the present invention: LCMS: 542 [M+H]+, RT=1.69 minutes

[0960] Compound 52 of the present invention: LCMS: 542 [M+H]+, RT = 1.80 minutes

[0961] Compound 53 of the present invention: LCMS: 552 [M+H]+, RT=1.66 minutes

[0962] Compound 54 of the present invention: LCMS: 524 [M+H] +, RT = 1.43 minutes Compound 55 of the present invention: LCMS: 540 [M+H] +, RT = 1.60 minutes

[0963] Compound 56 of the present invention: LCMS: 510 [M+H]+, RT=1.63 minutes

[0964] Compound 57 of the present invention: LCMS: 500 [M+H]+, RT = 1.60 min

[0965] Compound 58 of the present invention: LCMS: 526 [M+H]+, RT = 1.41 minutes

[0966] Compound 59 of the present invention: LCMS: 542 [M+H]+, RT = 1.57 minutes

[0967] Compound 60 of the present invention: LCMS: 512 [M+H]+, RT=1.49 minutes

[0968] Compound 61 of the present invention: LCMS: 528 [M+H]+, RT=1.71 minutes

[0969] Compound 62 of the present invention: LCMS: 494 [M+H]+, RT=1.40 min

[0970] Compound 63 of the present invention: LCMS: 510 [M+H]+, RT=1.57 minutes

[0971] Compound 64 of the present invention: LCMS: 500 [M+H]+, RT = 1.44 minutes

[0972] Compound 65 of the present invention: LCMS: 526 [M+H]+, RT = 1.44 minutes

[0973] Compound 66 of the present invention: LCMS: 542 [M+H]+, RT=1.60 min

[0974] Compound 67 of the present invention: LCMS: 543 [M+H]+, RT = 1.64 minutes

[0975] Compound 68 of the present invention: LCMS: 525 [M+H]+, RT = 1.48 minutes

[0976] Compound 69 of the present invention: LCMS: 541 [M+H]+, RT=1.65 minutes

[0977] Compound 70 of the present invention: LCMS: 487 [M+H]+, RT=1.62 minutes

[0978] Compound 71 of the present invention: LCMS: 503 [M+H]+, RT = 1.78 minutes

[0979] Compound 72 of the present invention: LCMS: 439 [M+H]+, RT = 1.59 minutes

[0980] Compound 73 of the present invention: LCMS: 455 [M+H]+, RT = 1.75 minutes

[0981] Compound 74 of the present invention: LCMS: 487 [M+H]+, RT = 1.64 minutes

[0982] Compound 75 of the present invention: LCMS: 503 [M+H]+, RT = 1.79 minutes

[0983] Compound 76 of the present invention: LCMS: 439 [M+H]+, RT = 1.60 minutes

[0984] Compound 77 of the present invention: LCMS: 455 [M+H]+, RT = 1.77 minutes

[0985] Next, examples of the compounds of the present invention produced according to any of the production examples described in the Examples and the production methods described in this specification are shown below.

[0986] [Chemical Formula 37]

[0987]

[0988] In the compound represented by formula (L-1) (hereinafter referred to as compound (L-1)), n is 0, R 1 is a hydrogen atom, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX1).

[0989] [Table 8]

[0990]

[0991]

[0992] [Table 9]

[0993]

[0994]

[0995] [Table 10]

[0996]

[0997]

[0998] [Table 11]

[0999]

[1000]

[1001] [Table 12]

[1002]

[1003]

[1004] [Table 13]

[1005]

[1006]

[1007] [Table 14]

[1008] [Table L13]

[1009] <![CDATA[5-OCF2H-1-Me-1H-pyrazol-3-yl]]> <![CDATA[3-OCF2H-1-Me-1H-pyrazol-4-yl]]> <![CDATA[5-OCF2H-1-Me-1H-pyrazol-4-yl]]> <![CDATA[3-OCF2H-1-Me-1H-pyrazol-5-yl]]> <![CDATA[4-OCF2H-1-Me-1H-pyrazol-5-yl]]> 2-F-1-Me-1H-imidazol-4-yl 2-Cl-1-Me-1H-imidazol-4-yl 2-Br-1-Me-1H-imidazol-4-yl

[1010] In compound (L-1), n ​​is 0, R 1 is methyl, R3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX4).

[1011] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX5).

[1012] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX6).

[1013] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX7).

[1014] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX8).

[1015] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX9).

[1016] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX10).

[1017] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX11).

[1018] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX12).

[1019] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX13).

[1020] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX14).

[1021] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX15).

[1022] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX16).

[1023] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX17).

[1024] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX18).

[1025] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX22).

[1026] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX23).

[1027] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX24).

[1028] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX25).

[1029] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX26).

[1030] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX27).

[1031] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a fluorine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX28).

[1032] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX29).

[1033] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX30).

[1034] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX31).

[1035] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX32).

[1036] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX33).

[1037] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX34).

[1038] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a fluorine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX35).

[1039] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a fluorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX36).

[1040] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX40).

[1041] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX41).

[1042] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX42).

[1043] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX43).

[1044] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX44).

[1045] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a chlorine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX45).

[1046] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX46).

[1047] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX47).

[1048] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX48).

[1049] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX49).

[1050] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX50).

[1051] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX51).

[1052] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a chlorine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX52).

[1053] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX53).

[1054] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a chlorine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX54).

[1055] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX58).

[1056] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX59).

[1057] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX60).

[1058] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX61).

[1059] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a bromine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX62).

[1060] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX63).

[1061] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX64).

[1062] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX65).

[1063] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX66).

[1064] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX67).

[1065] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX68).

[1066] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a bromine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX69).

[1067] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX70).

[1068] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX71).

[1069] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a bromine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX72).

[1070] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX76).

[1071] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX77).

[1072] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX78).

[1073] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is an iodine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX79).

[1074] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX80).

[1075] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX81).

[1076] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX82).

[1077] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX83).

[1078] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX84).

[1079] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX85).

[1080] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is an iodine atom, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX86).

[1081] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX87).

[1082] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX88).

[1083] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX89).

[1084] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is an iodine atom, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX90).

[1085] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX94).

[1086] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX95).

[1087] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is trifluoromethyl, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX96).

[1088] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX97).

[1089] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX98).

[1090] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX99).

[1091] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX100).

[1092] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX101).

[1093] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX102).

[1094] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is trifluoromethyl, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX103).

[1095] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX104).

[1096] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX105).

[1097] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX106).

[1098] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX107).

[1099] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX108).

[1100] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX112).

[1101] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is difluoromethyl, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX113).

[1102] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX114).

[1103] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX115).

[1104] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX116).

[1105] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX117).

[1106] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX118).

[1107] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX119).

[1108] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is difluoromethyl, R 3cThe compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX120).

[1109] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX121).

[1110] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX122).

[1111] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX123).

[1112] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX124).

[1113] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX125).

[1114] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is difluoromethyl, R 3c The compounds wherein is a hydrogen atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX126).

[1115] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX130).

[1116] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX131).

[1117] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX132).

[1118] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX133).

[1119] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX134).

[1120] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX135).

[1121] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX136).

[1122] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX137).

[1123] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX138).

[1124] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX139).

[1125] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX140).

[1126] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX141).

[1127] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX142).

[1128] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX143).

[1129] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX144).

[1130] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX148).

[1131] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX149).

[1132] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX150).

[1133] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX151).

[1134] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX152).

[1135] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX153).

[1136] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a fluorine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX154).

[1137] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX155).

[1138] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX156).

[1139] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX157).

[1140] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX158).

[1141] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX159).

[1142] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX160).

[1143] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a fluorine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX161).

[1144] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a fluorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX162).

[1145] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX166).

[1146] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX167).

[1147] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX168).

[1148] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX169).

[1149] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX170).

[1150] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a chlorine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX171).

[1151] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX172).

[1152] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX173).

[1153] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX174).

[1154] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX175).

[1155] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX176).

[1156] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX177).

[1157] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a chlorine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX178).

[1158] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX179).

[1159] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a chlorine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX180).

[1160] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX184).

[1161] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX185).

[1162] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX186).

[1163] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX187).

[1164] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a bromine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX188).

[1165] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX189).

[1166] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX190).

[1167] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX191).

[1168] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX192).

[1169] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX193).

[1170] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX194).

[1171] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a bromine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX195).

[1172] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX196).

[1173] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX197).

[1174] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a bromine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX198).

[1175] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX202).

[1176] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX203).

[1177] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX204).

[1178] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is an iodine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX205).

[1179] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX206).

[1180] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX207).

[1181] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX208).

[1182] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX209).

[1183] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX210).

[1184] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX211).

[1185] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is an iodine atom, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX212).

[1186] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX213).

[1187] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX214).

[1188] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX215).

[1189] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is an iodine atom, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX216).

[1190] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX220).

[1191] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX221).

[1192] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is trifluoromethyl, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX222).

[1193] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX223).

[1194] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX224).

[1195] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX225).

[1196] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX226).

[1197] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX227).

[1198] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX228).

[1199] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is trifluoromethyl, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX229).

[1200] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX230).

[1201] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX231).

[1202] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX232).

[1203] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX233).

[1204] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is trifluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX234).

[1205] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX238).

[1206] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is difluoromethyl, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX239).

[1207] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX240).

[1208] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX241).

[1209] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX242).

[1210] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX243).

[1211] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX244).

[1212] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX245).

[1213] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is difluoromethyl, R 3cThe compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX246).

[1214] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX247).

[1215] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX248).

[1216] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX249).

[1217] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX250).

[1218] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX251).

[1219] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is difluoromethyl, R 3c The compounds wherein is a fluorine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX252).

[1220] In compound (L-1), n ​​is 0, R 1 is methyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX256).

[1221] In compound (L-1), n ​​is 1, R 1 is methyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX257).

[1222] In compound (L-1), n ​​is 2, R 1 is methyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX258).

[1223] In compound (L-1), n ​​is 0, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX259).

[1224] In compound (L-1), n ​​is 1, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX260).

[1225] In compound (L-1), n ​​is 2, R 1 is ethyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX261).

[1226] In compound (L-1), n ​​is 0, R 1 is isopropyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX262).

[1227] In compound (L-1), n ​​is 1, R 1 is isopropyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX263).

[1228] In compound (L-1), n ​​is 2, R 1 is isopropyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX264).

[1229] In compound (L-1), n ​​is 0, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX265).

[1230] In compound (L-1), n ​​is 1, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX266).

[1231] In compound (L-1), n ​​is 2, R 1 is methyl cyano, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX267).

[1232] In compound (L-1), n ​​is 0, R 1 is benzyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX268).

[1233] In compound (L-1), n ​​is 1, R 1 is benzyl, R 3b is a hydrogen atom, R 3c The compounds wherein is a bromine atom, and Q is any substituent described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX269).

[1234] In compound (L-1), n ​​is 2, R 1 is benzyl, R 3b is a hydrogen atom, R 3cThe compounds wherein is a bromine atom, and Q is any substitue...

Claims

1. A compound represented by formula (I) or an N-oxide thereof, [Chemical formula 1] In formula (I), W represents an oxygen atom or a sulfur atom, R 1 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group D, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group E, a phenyl group which may be substituted by one or more substituents selected from group F, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group F, C(O)R 4 、C(O)OR 4 or C(O)NR 4 R 5 , R 4 and R 5 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from group F, a 5- or 6-membered heterocyclic group which may be substituted by one or more substituents selected from group F, or a hydrogen atom, R 2 represents a C1-C6 alkyl group, a cyclopropyl group, a cyclopropylmethyl group or an NR 6 R 7 , R 6 and R 7 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, or a hydrogen atom; or R 6 and R 7 Together with the nitrogen atom to which they are bound, they may form an aziridinyl, azetidinyl, pyrrolidinyl or piperidinyl group, n represents 0, 1 or 2, G 1 Represents nitrogen atom or CR 3a , G 2 Represents nitrogen atom or CR 3b , G 3 Represents nitrogen atom or CR 3c , G 4 Represents nitrogen atom or CR 3d , R 3a , R 3b , R 3c and R 3d are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group H, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group J, a phenyl group which may be substituted by one or more substituents selected from group K, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group K, OR 8 NR 8 R 9 NR 8a R 9a NR 10 NR 8 R 9 NR 10 OR 9 NR 9 C(O)R 11 NR 10 NR 9 C(O)R 11 NR 9 C(O)OR 12 NR 10 NR 9 C(O)OR 12 NR 9 C(O)NR 13 R 14 NR 10 NR 9 C(O)NR 13 R 14 、N=CHNR 13 R 14 、N=S(O) p R 15 R 16 、C(O)R 11 、C(O)OR 17 、C(O)NR 13 R 14 、C(O)NR 9 S(O)2R 18 , CR 19 =NOR 17 NR 9 CR 10 =NOR 17 、S(O) m R 18 , cyano group, nitro group, hydrogen atom or halogen atom, p represents 0 or 1, m represents 0, 1 or 2, R 8 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group L, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group M, a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from group M, a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group J 2 Phenyl substituted with one or more substituents, which may be selected from Group J 2 6-membered aromatic heterocyclic group substituted with one or more substituents, hydrogen atom or S(O)2R 18 , R 11 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, a C1-C3 alkyl group which may be selected from the group J 2 Phenyl substituted with one or more substituents, which may be selected from Group J 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a hydrogen atom, R 12 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl part in the phenyl C1-C3 alkyl group may be selected from the group J 2 substituted with one or more substituents in}, R 13 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R 14 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from the group L, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group M, S(O)2R 18 or hydrogen atoms, R 15 and R 16 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms, R 17 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, which may be selected from Group J 2 phenyl substituted with one or more substituents, or a hydrogen atom, R 18 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or may be selected from Group J 2 A phenyl group substituted with one or more substituents, R 19 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or OR 20 NR 21 R 22 or hydrogen atoms, R 20 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 9 , R 10 , R 21 and R 22 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom, R 8a and R 9a Together with the nitrogen atom to which they are bonded, they form a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from group P, Q is for Q 1 or Q 2 , [Chemical formula 2] Z 1 Indicates NR 3j , oxygen atoms or sulfur atoms, Z 2 Indicates NR 3k , oxygen atoms or sulfur atoms, In Q for Q 1 And Z 1 Indicates NR 3j In the case of X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 3 Represents nitrogen atom or CR 3g , In Q for Q 1 And Z 1 In the case of an oxygen atom, X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 3 Represents nitrogen atom or CR 3g (in, Excluding the existing X 1 , X 2 and X 3 All represent nitrogen atoms), In Q for Q 1 And Z 1 In the case of a sulfur atom, X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 3 Represents nitrogen atom or CR 3g (excluding the existing X 1 , X 2 and X 3 All represent nitrogen atoms), In Q for Q 2 And Z 2 Indicates NR 3k In the case of X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 4 Represents nitrogen atom or CR 3h , In Q for Q 2 And Z 2 In the case of an oxygen atom, X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 4 Represents nitrogen atom or CR 3h (excluding the existing X 1 , X 2 and X 4 All represent nitrogen atoms), In Q for Q 2 And Z 2 In the case of a sulfur atom, X 1 Represents nitrogen atom or CR 3e , X 2 Represents nitrogen atom or CR 3f , X 4 Represents nitrogen atom or CR 3h (excluding the existing X 1 , X 2 and X 4 All represent nitrogen atoms), R 3j represents a methyl group which may be substituted with one or more substituents selected from group T, a C2-C4 chain hydrocarbon group which may be substituted with one or more substituents selected from group U, a C5-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group V, a C5-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group K 2 C3-C7 cycloalkyl substituted with one or more substituents selected from Group X, phenyl which may be substituted with one or more substituents selected from Group X, 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group X, C(O)R 23 、C(O)OR 24 、C(O)NR 25 R 26 、C(O)NR 27 S(O)2R 28 , CR 29 =NOR 24 or S(O) k R 28 , k represents 0, 1 or 2, R 23 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group X, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group X, or a hydrogen atom, R 24 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group X, or a hydrogen atom, R 25 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R 26 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group V, which may be selected from Group K 2 C3-C7 cycloalkyl substituted with one or more substituents, S(O) v R 28 or hydrogen atoms, v represents 0, 1 or 2, R 28 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from Group X, R 29 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or OR 30 NR 31 R 32 or hydrogen atoms, R 30 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 27 , R 31 and R 32 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom, R 3k represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group Y, which may be selected from group M 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group A 2 The phenyl group substituted with one or more substituents in the group A 2 substituted with one or more substituents in 5- or 6-membered aromatic heterocyclic group, C(O)R 52 、C(O)OR 53 、C(O)NR 54 R 55 、C(O)NR 56 S(O)2R 57 , CR 58 =NOR 53 、S(O) t R 57 or hydrogen atoms, t represents 0, 1 or 2, R 52 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, a C1-C3 alkyl group which may be selected from Group A 2 The phenyl group substituted with one or more substituents in the group A 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a hydrogen atom, R 53 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may be selected from Group A 2 phenyl substituted with one or more substituents, or a hydrogen atom, R 54 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R 55 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group Y, which may be selected from group M 2 C3-C7 cycloalkyl substituted with one or more substituents, S(O) y R 28 or hydrogen atoms, y represents 0, 1 or 2, R 57 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or may be selected from Group A 2 A phenyl group substituted with one or more substituents, R 58 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or OR 59 NR 60 R 61 or hydrogen atoms, R 59 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 56 , R 60 and R 61 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom, R 3e , R 3f , R 3g and R 3h The same or different from each other, indicating that they can be selected from group B 2 A C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from Group D 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group E 2 The phenyl group substituted with one or more substituents in the group E 2 substituted with one or more substituents in 5- or 6-membered aromatic heterocyclic group, OR 33 NR 33 R 34 NR 33a R 34a NR 35 NR 33 R 34 NR 35 OR 34 NR 34 C(O)R 36 NR 35 NR 34 C(O)R 36 NR 34 C(O)OR 37 NR 35 NR 34 C(O)OR 37 NR 34 C(O)NR 38 R 39 NR 35 NR 34 C(O)NR 38 R 39 、N=CHNR 38 R 39 、N=S(O) q R 40 R 41 、C(O)R 36 、C(O)OR 42 、C(O)NR 38 R 39 、C(O)NR 34 S(O)2R 43 , CR 44 =NOR 42 NR 34 CR 35 =NOR 42 、S(O) r R 43 , cyano, nitro, halogen or hydrogen atoms, q represents 0 or 1, r represents 0, 1 or 2, R 33 Indicates that it can be selected from group B 2 A C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from Group D 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from group D 2 C3-C7 cycloalkenyl substituted with one or more substituents, which may be selected from Group E 2 The phenyl group substituted with one or more substituents in the group E 2 6-membered aromatic heterocyclic group substituted with one or more substituents, hydrogen atom or S(O)2R 43 , R 36 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, a C1-C3 alkyl group which may be selected from Group E 2 The phenyl group substituted with one or more substituents in the group E 2 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a hydrogen atom, R 37 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl part of the phenyl C1-C3 alkyl group may be selected from the group E 2 substituted with one or more substituents in}, R 38 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R 39 Indicates that it can be selected from group B 2 A C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from Group D 2 C3-C7 cycloalkyl substituted with one or more substituents, S(O)2R 43 or hydrogen atoms, R 40 and R 41 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms, R 42 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may be selected from Group E 2 phenyl substituted with one or more substituents, or a hydrogen atom, R 43 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or may be selected from Group E 2 A phenyl group substituted with one or more substituents, R 44 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, or OR 45 NR 46 R 47 or hydrogen atoms, R 45 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 34 , R 35 , R 46 and R 47 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom, R 33a and R 34a Together with the nitrogen atom to which they are bound, they form a 2 A 3-7 membered non-aromatic heterocyclic group substituted with one or more substituents in Group D: C3-C6 cycloalkyl which may be substituted with one or more substituents selected from the group consisting of halogen atoms and C1-C3 alkyl, C1-C6 alkoxy which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl which may be substituted with one or more halogen atoms, C2-C6 alkyloxycarbonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C2-C6 alkyl ...1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted with one 2 The phenyl group substituted with one or more substituents in the group L 2 A group consisting of a 5- or 6-membered aromatic heterocyclic group, a hydroxyl group, a cyano group and a halogen atom substituted with one or more substituents in Group E: the group consisting of C1-C6 alkyl groups which may be substituted by one or more halogen atoms, C1-C6 alkoxy groups which may be substituted by one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted by one or more halogen atoms, and halogen atoms, Group F: the group consisting of C1-C6 alkyl which may be substituted by one or more halogen atoms, C1-C6 alkoxy which may be substituted by one or more halogen atoms, C1-C6 alkylsulfanyl which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted by one or more halogen atoms, C1-C6 alkylamino which may be substituted by one or more halogen atoms, di(C1-C6 alkyl)amino, C2-C6 alkylcarbonyl which may be substituted by one or more halogen atoms, C2-C6 alkoxycarbonyl which may be substituted by one or more halogen atoms, hydroxyl, sulfanyl, amino, cyano, nitro and halogen atoms. Group H: the group consisting of C1-C6 alkoxy which may be substituted by one or more halogen atoms, C3-C6 alkenyloxy which may be substituted by one or more halogen atoms, C3-C6 alkynyloxy which may be substituted by one or more halogen atoms, C1-C6 alkylsulfanyl which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted by one or more halogen atoms, C3-C6 cycloalkyl which may be substituted by one or more halogen atoms, cyano, hydroxyl and halogen atoms, Group J: the group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group, Group K: C1-C6 alkyl which may be substituted with one or more halogen atoms, which may be selected from Group J 2 substituted with one or more substituents in 5- or 6-membered aromatic heterocyclic group, OR 49 NR 48 R 49 、C(O)R 49 、C(O)NR 48 R 49 、OC(O)R 48 、OC(O)OR 48 NR 49 C(O)R 48 NR 49 C(O)OR 48 、C(O)OR 49 , a group consisting of a halogen atom, a nitro group, a cyano group and an amino group, R 48 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, R 49 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, or a hydrogen atom, Group L: C1-C6 alkoxy which may be substituted with one or more halogen atoms, which may be selected from Group J 2 Phenyl substituted with one or more substituents, which may be selected from Group J 2 A 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be selected from the group consisting of 2 3-7 membered non-aromatic heterocyclic group, amino group, NHR group substituted with one or more substituents 50 NR 50 R 51 , a group consisting of a halogen atom and a cyano group, R 50 and R 51 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms, Group M: a group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group, Group P: the group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group, Group T: a group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, and a halogen atom. Group U: a group consisting of a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a sulfanyl group and a fluorine atom, Group V: a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, a cyano group and a halogen atom. Group X: the group consisting of C1-C6 alkyl which may be substituted by one or more halogen atoms, C1-C6 alkoxy which may be substituted by one or more halogen atoms, C1-C6 alkylsulfanyl which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl which may be substituted by one or more halogen atoms, C1-C6 alkylamino which may be substituted by one or more halogen atoms, di(C1-C6 alkyl)amino which may be substituted by one or more halogen atoms, C2-C6 alkylcarbonyl which may be substituted by one or more halogen atoms, C2-C6 alkoxycarbonyl which may be substituted by one or more halogen atoms, hydroxyl, sulfanyl, amino, cyano, nitro and halogen atoms. Group Y: a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, a cyano group and a halogen atom. Group A 2 : the group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom, Group B 2 : a C3-C6 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms, a hydroxyl group, a sulfanyl group, a cyano group and a halogen atom, Group D 2 : a group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a halogen atom, Group E 2 : the group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom, Group F 2 : the group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group, Group H 2 : a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, and a halogen atom, Group J 2 : C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, hydroxyl group, C1-C6 alkoxy group which may be substituted by one or more halogen atoms, C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, sulfanyl group, C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, amino group, NHR 50 NR 50 R 51 、C(O)R 50 、OC(O)R 50 、C(O)OR 50 , cyano, nitro and halogen atoms, Group K 2 : a group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a fluorine atom, Group L 2 : the group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylamino group which may be substituted by one or more halogen atoms, a di(C1-C6 alkyl)amino group, a C2-C6 alkylcarbonyl group which may be substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group which may be substituted by one or more halogen atoms, a hydroxyl group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom, Group M 2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, and a halogen atom.

2. The compound or N-oxide thereof according to claim 1, wherein G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a nitrogen atom or CR 3d .

3. The compound or N-oxide thereof according to claim 1, wherein G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d .

4. The compound or N-oxide thereof according to any one of claims 1 to 3, wherein Q for Q 1 , in Q 1 In, Z 1 , X 1 , X 2 and X 3 The combination is: Z 1 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g combination of; Z 1 is an oxygen atom, X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g combination of; Z 1 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 3 is a combination of nitrogen atoms; Z 1 is a sulfur atom, X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g combination of; Z 1 is a sulfur atom, X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g combination of; Z 1 NR 3j , X 1 is a nitrogen atom, X 2 CR 3f , X 3 CR 3g combination of; Z 1 NR 3j , X 1 CR 3e , X 2 is a nitrogen atom, X 3 CR 3g or, Z 1 NR 3j , X 1 CR 3e , X 2 CR 3f , X 3 A combination of nitrogen atoms.

5. The compound or N-oxide thereof according to any one of claims 1 to 3, wherein Q for Q 2 , in Q 2 In, Z 2 , X 1 , X 2 and X 4 The combination is: Z 2 is an oxygen atom, X 1 is a nitrogen atom, X 2 CR 3f , X 4 CR 3h combination of; Z 2 is an oxygen atom, X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h combination of; Z 2 is an oxygen atom, X 1 CR 3e , X 2 CR 3f , X 4 is a combination of nitrogen atoms; Z 2 NR 3k , X 1 is a nitrogen atom, X 2 CR 3f , X 4 CR 3h combination of; Z 2 NR 3k , X 1 CR 3e , X 2 is a nitrogen atom, X 4 CR 3h combination of; Z 2 NR 3k , X 1 CR 3e , X 2 CR 3f , X 4 is a combination of nitrogen atoms; Z 2 NR 3k , X 1 CR 3e , X 2 CR 3f , X 4 CR 3h or, Z 2 NR 3k , X 1 is a nitrogen atom, X 2 is a nitrogen atom, X 4 CR 3h combination.

6. The compound or N-oxide thereof according to any one of claims 1 to 5, wherein R 2 It is ethyl.

7. The compound or N-oxide thereof according to any one of claims 1 to 6, wherein W is an oxygen atom. 8 . A harmful arthropod control composition comprising the compound according to claim 1 or an N-oxide thereof.

9. A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound or N-oxide thereof according to any one of claims 1 to 7, Group (a): a group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): fungicidal active ingredients; Group (c): plant growth regulating ingredients; Group (d): repellent ingredients.

10. A method for controlling harmful arthropods, wherein: An effective amount of the compound or N-oxide thereof according to any one of claims 1 to 7 or an effective amount of the composition according to claim 9 is applied to a harmful arthropod or a habitat of a harmful arthropod.

11. A seed or a vegetative propagation organ, which holds an effective amount of the compound according to any one of claims 1 to 7 or an N-oxide thereof, or an effective amount of the composition according to claim 9.

12. A compound represented by formula (II) or a salt thereof, [Chemical formula 3] In formula (II), the symbols have the same meanings as in claim 1.

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